CN102786372A - Synthesis of m-nitrobenzaldehyde derivative - Google Patents
Synthesis of m-nitrobenzaldehyde derivative Download PDFInfo
- Publication number
- CN102786372A CN102786372A CN2011104624871A CN201110462487A CN102786372A CN 102786372 A CN102786372 A CN 102786372A CN 2011104624871 A CN2011104624871 A CN 2011104624871A CN 201110462487 A CN201110462487 A CN 201110462487A CN 102786372 A CN102786372 A CN 102786372A
- Authority
- CN
- China
- Prior art keywords
- solvent
- reaction
- nitrobenzaldehyde
- group
- nitrating agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title abstract description 4
- 238000003786 synthesis reaction Methods 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000003935 benzaldehydes Chemical class 0.000 claims abstract description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 13
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 11
- -1 auch as -F Chemical group 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 230000000802 nitrating effect Effects 0.000 claims description 16
- 239000002904 solvent Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 108010016626 Dipeptides Proteins 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000003172 aldehyde group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 abstract 1
- 239000000126 substance Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000010813 municipal solid waste Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- RNYZJZKPGHQTJR-UHFFFAOYSA-N protoanemonin Chemical compound C=C1OC(=O)C=C1 RNYZJZKPGHQTJR-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical class COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IONMUCYQDGALHX-UHFFFAOYSA-N formaldehyde;1-phenylethanone Chemical compound O=C.CC(=O)C1=CC=CC=C1 IONMUCYQDGALHX-UHFFFAOYSA-N 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthesis of a m-nitrobenzaldehyde derivative, can be used for preparing a plurality of m-nitrobenzaldehyde derivatives. The method takes benzaldehyde and its derivative as initial raw materials and comprises the following steps: reacting with ammonia water to generate tri(substituted benzaldehyde) dipeptide, reacting tri (substituted benzaldehyde) dipeptide with a nitrated reagent, then hydrolysizing to obtain the m-nitrobenzaldehyde derivative, and a chemical structure comprises is shown as follows: in the formula, R group can be hydrogen, or electron-donating group, such as -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -OH, -NH2, -OR ', -NHR ' and the like, wherein R' is -CH3, -CH2CH3, -COCH3 and the like; or electron-withdrawing group, auch as -F, -Cl, -Br, -CF3, -CCl3, -N(CH3)3<+>, -NO2, -CN, -SO3H, -COCH3, -COOH, -COOCH3, -CONH2, -NH3<+> and the like, R group is a substituent, two substituents or three substituents; and R group can be in the adjacent position, the meta position or the contraposition of an aldehyde group. The reaction condition is mild and the yield is high.
Description
Technical field:
The invention belongs to a kind of method of synthetic replacement m-nitrobenzaldehyde; Relating to the substituted benzoyl aldehyde derivatives specifically is starting raw material; Earlier generate three (substituted benzaldehydes) diamino that contracts,, make the method for m-nitrobenzaldehyde verivate through hydrolysis then with the nitrating agent reaction with the ammoniacal liquor reaction.
Background technology:
M-nitrobenzaldehyde is a kind of important medicinal intermediates.Like compound 1 is Synthetic 2-amino-3, the midbody of 4-dihydro-6-methyl-(4-pyridine sulfydryl) quinazoline-4-one, and compound 2 is paeonol derivative (Lai Puhui; Field radiance, Zhao Hua. a kind of synthetic and anti-microbial activity [J] of paeonol derivative. Wuhan University's journal (version of science), 2010; 56 (5): synthesis material 523～526), compound 3 are protoanemonin verivate (Sun Haiyan, Xue Feiqun; Zhang Lifang; Deng. the synthetic and bacteriostatic activity [J] of protoanemonin verivate. Chinese veterinary science, 2008,38 (07): synthesis material 626～628).
Summary of the invention:
The problem that the present invention will solve provides a kind of method of synthetic m-nitrobenzaldehyde verivate, and some product wherein can be converted into important medicinal intermediates.
Compound involved in the present invention has following general structure:
The R base can be a hydrogen in the formula; Perhaps donor residues, as :-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2,-OH ,-NH
2,-OR ' ,-NHR ' etc., wherein R ' is-CH
3,-CH
2CH
3,-COCH
3Deng; Perhaps electron withdrawing group, as :-F ,-Cl ,-Br ,-CF
3,-CCl
3,-N (CH
3)
3 +,-NO
2,-CN ,-SO
3H ,-COCH
3,-COOH ,-COOCH
3,-CONH
2,-NH
3 +Deng, the R base is 1 substituting group, 2 substituting groups or 3 substituting groups; The R base can be positioned at ortho position, a position or the contraposition of aldehyde radical.
The inventive method is to be that the reaction of raw material and ammoniacal liquor generates three (substituted benzaldehydes) diamino (being called for short TSBADA) that contracts with substituted benzaldehyde (SBA), carries out nitration reaction with nitrating agent then, and last hydrolysis generates the m-nitrobenzaldehyde verivate.Wherein the molar ratio of material of substituted benzaldehyde and ammoniacal liquor is 1: 0.1 to 1: 80; The mass ratio of substituted benzaldehyde and solvent is 1: 2 to 1: 1000; Reaction times is 0.5～24h, and temperature of reaction is 20～160 ℃: recommending the molar ratio of material of substituted benzaldehyde and ammoniacal liquor is 1: 0.1 to 1: 60; The molar ratio of material of TSBADA and nitrating agent is 1: 2 to 1: 100, and nitrating agent is the mixture of the concentrated nitric acid and the vitriol oil, the ethanoyl nitric ether; The mixture of nitric acid and acetic anhydride; Organic nitrates or nitrogen oxides, the mass ratio of substituted benzaldehyde and solvent are 1: 2 to 1: 1000, and the reaction times is 1～10h; Temperature of reaction is 40～150 ℃: recommending the molar ratio of material of TSBADA and nitrating agent is 1: 2 to 1: 5; The mass ratio of substituted benzaldehyde and solvent is 1: 3 to 1: 100, and the reaction times is 2～5h, and temperature of reaction is 50～120 ℃.
Solvent described in the inventive method is water or organic solvent, organic solvent such as benzene, toluene, oil of mirbane, ether, acetone, chloroform, tetracol phenixin, THF; Or above-mentioned any two kinds or above solvent are with the miscible mixed solvent of arbitrary proportion.
Embodiment
To help to understand the present invention through following embodiment, but not limit content of the present invention.
Embodiment 1: in being cooled to 10 ℃ phenyl aldehyde, drip the 90ml massfraction and be 25% ammoniacal liquor, be warming up to 40 ℃ after dropwising, insulation reaction 12 hours.After question response stops, being cooled to room temperature earlier, filtering then, wash, drying, white product TSBADA.Get massfraction and be 95% vitriol oil 27g, nitrosonitric acid 8.5g prepares nitrating agent under cryosel bath condition, for use.Following 5g TSBADA slowly joins in the nitrating agent in cryosel bath condition, and reinforced finishing slowly is warming up to 80 ℃, reaction 4h.Reaction finishes postcooling to room temperature, then reaction solution is transferred to magnetic agitation 1h in the beaker that trash ice is housed.
With the reaction solution vacuum filtration, to neutral, get faint yellow crude product with the distilled water wash filter cake, ir lamp is dry down.Products therefrom is purified through the method for recrystallization and activated carbon decolorizing, and solvent is toluene-sherwood oil mixed solvent (volume ratio is 2: 1), and obtain white through purifying glossiness 3, the 5-dinitrobenzal-dehyde.
Embodiment 2: to be cooled to 10 ℃ between to drip the 90ml massfraction in the sulfonic benzo formaldehyde be 25% ammoniacal liquor, be warming up to 40 ℃ after dropwising, insulation reaction 12 hours.After question response stops, being cooled to room temperature earlier, filtering then, wash, drying, white product TSBADA.Get massfraction and be 95% vitriol oil 27g, nitrosonitric acid 8.5g prepares nitrating agent under cryosel bath condition, for use.A following 5gTSBADA slowly joins in the nitrating agent in cryosel bath condition, and reinforced finishing slowly is warming up to 80 ℃, reaction 4h.Reaction finishes postcooling to room temperature, then reaction solution is transferred to magnetic agitation 1h in the beaker that trash ice is housed.
With the reaction solution vacuum filtration, to neutral, get faint yellow crude product with the distilled water wash filter cake, ir lamp is dry down.Products therefrom is purified through the method for recrystallization and activated carbon decolorizing, and solvent is toluene-sherwood oil mixed solvent (volume ratio is 2: 1), obtains white glossiness 3-aldehyde radical-5-nitrobenzene-sulfonic acid through purifying.
Embodiment 3: to be cooled to 10 ℃ between to drip the 90ml massfraction in the cyanobenzaldehyde be 25% ammoniacal liquor, be warming up to 40 ℃ after dropwising, insulation reaction 12 hours.After question response stops, being cooled to room temperature earlier, filtering then, wash, drying, white product TSBADA.Get massfraction and be 95% vitriol oil 27g, nitrosonitric acid 8.5g prepares nitrating agent under cryosel bath condition, for use.A following 5gTSBADA slowly joins in the nitrating agent in cryosel bath condition, and reinforced finishing slowly is warming up to 80 ℃, reaction 4h.Reaction finishes postcooling to room temperature, then reaction solution is transferred to magnetic agitation 1h in the beaker that trash ice is housed.
With the reaction solution vacuum filtration, to neutral, get faint yellow crude product with the distilled water wash filter cake, ir lamp is dry down.Products therefrom is purified through the method for recrystallization and activated carbon decolorizing, and solvent is toluene-sherwood oil mixed solvent (volume ratio is 2: 1), obtains white glossiness 3-cyanic acid-5-nitrobenzaldehyde through purifying.
Embodiment 4: to be cooled to 10 ℃ between to drip the 90ml massfraction in the acetylbenzene formaldehyde be 25% ammoniacal liquor, be warming up to 40 ℃ after dropwising, insulation reaction 12 hours.After question response stops, being cooled to room temperature earlier, filtering then, wash, drying, white product TSBADA.Get massfraction and be 95% vitriol oil 27g, nitrosonitric acid 8.5g prepares nitrating agent under cryosel bath condition, for use.A following 5gTSBADA slowly joins in the nitrating agent in cryosel bath condition, and reinforced finishing slowly is warming up to 80 ℃, reaction 4h.Reaction finishes postcooling to room temperature, then reaction solution is transferred to magnetic agitation 1h in the beaker that trash ice is housed.
With the reaction solution vacuum filtration, to neutral, get faint yellow crude product with the distilled water wash filter cake, ir lamp is dry down.Products therefrom is purified through the method for recrystallization and activated carbon decolorizing, and solvent is toluene-sherwood oil mixed solvent (volume ratio is 2: 1), obtains white glossiness 3-ethanoyl 5-nitrobenzaldehyde through purifying.
Claims (7)
1. the compound method of a m-nitrobenzaldehyde is that raw material and ammoniacal liquor generate three (substituted benzaldehydes) diamino (TSBADA) that contracts with the substituted benzaldehyde, and again with nitrating agent generation nitration reaction, last hydrolysis generates the m-nitrobenzaldehyde verivate, and reaction formula is as follows:
The molar ratio of material of raw material substituted benzaldehyde and ammoniacal liquor is 1: 0.1 to 1: 80;
The molar ratio of material of TSBADA and nitrating agent is 1: 2 to 1: 100;
Nitrating agent is concentrated nitric acid and the vitriol oil, diacetyl oxide, acetate one or more mixing wherein;
The mass ratio of substituted benzaldehyde and solvent is 1: 2 to 1: 1000;
Reaction times is 0.5～24h;
Temperature of reaction is 20～160 ℃.
2. of method in the claim 1, it is characterized in that the R base can be a hydrogen; Perhaps donor residues, as :-CH
3,-CH
2CH
3,-CH
2CH
2CH
3,-CH (CH
3)
2,-OH ,-NH
2,-OR ' and-NHR ', wherein R ' is-CH
3,-CH
2CH
3,-COCH
3Deng; Perhaps electron withdrawing group, as :-F ,-Cl ,-Br ,-CF
3,-CCl
3,-CN ,-N (CH
3)
3 +,-NO
2,-SO
3H ,-COCH
3,-COOH ,-COOCH
3,-CONH
2,-NH
3 +Deng.
3. of method in the claim 2, it is characterized in that the R base can be 1,2 or 3 substituting groups.
4. of method in the claim 3, it is characterized in that the R base can be positioned at ortho position, a position or the contraposition of aldehyde radical.
5. of method in the claim 1, it is characterized in that solvent is water or organic solvent.
6. of method in the claim 4, it is characterized in that solvent can be single inert solvent or mixed inert solvent during for organic solvent.
7. of method in the claim 6, it is characterized in that list-inert solvent can be benzene, toluene, oil of mirbane, ether, acetone, chloroform, tetracol phenixin, THF; The mixed inert solvent can be wherein any two kinds or above miscible with arbitrary proportion of benzene, toluene, oil of mirbane, ether, acetone, chloroform, tetracol phenixin, THF.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104624871A CN102786372A (en) | 2011-12-30 | 2011-12-30 | Synthesis of m-nitrobenzaldehyde derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104624871A CN102786372A (en) | 2011-12-30 | 2011-12-30 | Synthesis of m-nitrobenzaldehyde derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102786372A true CN102786372A (en) | 2012-11-21 |
Family
ID=47151982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011104624871A Pending CN102786372A (en) | 2011-12-30 | 2011-12-30 | Synthesis of m-nitrobenzaldehyde derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102786372A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL68257A (en) * | 1982-04-01 | 1985-09-29 | Bayer Ag | Preparation of o-nitro-benzaldehyde |
| CN101323575A (en) * | 2007-06-15 | 2008-12-17 | 南京理工大学 | Synthetic method of nitrobenzene methyl aldehyde |
-
2011
- 2011-12-30 CN CN2011104624871A patent/CN102786372A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL68257A (en) * | 1982-04-01 | 1985-09-29 | Bayer Ag | Preparation of o-nitro-benzaldehyde |
| CN101323575A (en) * | 2007-06-15 | 2008-12-17 | 南京理工大学 | Synthetic method of nitrobenzene methyl aldehyde |
Non-Patent Citations (2)
| Title |
|---|
| 丁成荣等: "间硝基苯甲醛合成新工艺的研究", 《浙江工业大学学报》, vol. 33, no. 6, 31 December 2005 (2005-12-31), pages 605 - 607 * |
| 黄银华等: "间硝基苯甲醛的合成工艺", 《石油化工》, vol. 37, no. 1, 1 July 2008 (2008-07-01), pages 1 - 1 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1151211A3 (en) | Method of obtaining 5-aroyl-1,2-dihydro-3h-pyrrole /1,2-a/-pyrrole-1-carboxylic acid | |
| TR201816203T4 (en) | Method for producing substituted (z) -alpha-fluoro-beta-amino-acrylaldehydes. | |
| CN102491906A (en) | Synthetic method for 2-methyl-3-trifluoromethyl phenylamine | |
| CN103613498B (en) | The synthetic method of Win-35833 | |
| JP2020026424A (en) | Method for synthesizing diclofenac sodium | |
| Alinezhad et al. | Protic pyridinium ionic liquid: As an efficient, green and environmentally friendly catalyst for the one-pot synthesis of amidoalkyl naphthol derivatives | |
| CN102786372A (en) | Synthesis of m-nitrobenzaldehyde derivative | |
| CN102391061A (en) | Method for preparing diaryl amine compound from 3-methyl dehydroshikimate | |
| CN106748796B (en) | The method for preparing the fluoro- 2,4- dinitrobenzene of 1,5- bis- | |
| Heidelberger | The Synthesis of DL-tryptophan-[beta]-C14, Indole-3-acetic Acid-[alpha]-C14 and DL-tryptophan-3-C14 | |
| CN111635301A (en) | Novel photoinitiator and preparation method thereof | |
| CN103497162B (en) | The synthetic method of 2-(4,6-dimethyl pyrimidine-2-base carbamoylamino alkylsulfonyl) methyl benzoate | |
| US3178478A (en) | 2-amino-5-halo-indanes | |
| CN106588698B (en) | A kind of preparation method of the third ammonium aldehyde of N-Boc biphenyl | |
| CN104909994A (en) | Method for synthesizing ciprofibrate intermediate and the intermediate | |
| Shriner et al. | The Structure of the Nitration Products of 9-Phenylxanthylium Salts1 | |
| CN113372231A (en) | Preparation method of 5-amino-1, 2, 3-benzenetricarboxylic acid | |
| JPH02223542A (en) | Preparation of hydroatropic acid derivative and ester thereof | |
| CN103992238A (en) | Preparation method of 3-aminosalicylic acid | |
| US3081314A (en) | Process for preparing 3, 4-dimethoxy-toluquinone | |
| CN103980127A (en) | Preparation method for oxyfluorfen | |
| CN112409248B (en) | 3-pyridine formamidine derivative and catalytic synthesis method thereof | |
| Li | Microwave-assisted synthesis of asymmetric thiocarbonohydrazones under solvent-free conditions | |
| Habibi et al. | Nitration of substituted phenols by different efficient heterogeneous systems | |
| Ungnade et al. | The Preparation of m-Hydroxybenzoic Acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DD01 | Delivery of document by public notice |
Addressee: Kang Congmin Document name: Notification of Acceptance of Patent Application |
|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20121121 |