GB879576A - Improvements in and relating to alkanoic acids and salts thereof - Google Patents
Improvements in and relating to alkanoic acids and salts thereofInfo
- Publication number
- GB879576A GB879576A GB27567/58A GB2756758A GB879576A GB 879576 A GB879576 A GB 879576A GB 27567/58 A GB27567/58 A GB 27567/58A GB 2756758 A GB2756758 A GB 2756758A GB 879576 A GB879576 A GB 879576A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- general formula
- compounds
- hydrogen
- group
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title abstract 5
- 150000007513 acids Chemical class 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 230000002152 alkylating effect Effects 0.000 abstract 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical class CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- -1 methoxy, 3,4-methylendioxy Chemical group 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 abstract 1
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 abstract 1
- LNAKGCAGKDRWTQ-UHFFFAOYSA-N 3-hydroxyimino-2-phenylbutanenitrile Chemical compound N(O)=C(C(C#N)C1=CC=CC=C1)C LNAKGCAGKDRWTQ-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- YPQUPBBEDDHCNC-UHFFFAOYSA-N diethyl 2-(cyanomethyl)-2-phenylpropanedioate Chemical compound CCOC(=O)C(CC#N)(C(=O)OCC)C1=CC=CC=C1 YPQUPBBEDDHCNC-UHFFFAOYSA-N 0.000 abstract 1
- DHRZNYVSWZTZMD-UHFFFAOYSA-N ethyl 2-cyano-2-(4-methoxyphenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=CC=C(OC)C=C1 DHRZNYVSWZTZMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises acids and esters of the general formula <FORM:0879576/IV (b)/1> (wherein R1 represents a hydrogen atom or a C1-4 alkyl group, R2 represents a hydrogen atom or a group COOR1, R3, R4 and R5 each represents a hydrogen atom or a C1-4 alkyl group, Ar represents a phenyl group which is unsubstituted or substituted by halogen atoms or methyl, methoxy, 3,4-methylendioxy or hydroxy groups, and n is 0, 1, 2 or 3, at least one of R1, R2 and R3 being other than hydrogen when n is 0) and salts of the above acids, e.g. derived from sodium and calcium hydroxide, and acid addition salts of the above acids and esters, e.g. prepared from inorganic and organic acids such as hydrochloric, hydrobromic, phosphoric, acetic, benzoic, tartaric, citric and methanesulphonic acids, and the preparation thereof by: (a) (when R2 is hydrogen) catalytically reducing an oxime of the general formula <FORM:0879576/IV (b)/2> (wherein X represents COOH) and, if desired, alkylating and esterifying the product; (b) (when R4 is hydrogen) catalytically hydrogenating a compound of the general formula <FORM:0879576/IV (b)/3> (wherein R11 represents a C1-4 alkyl group and R21 a hydrogen atom or a group COOR11) and, if desired, monoalkylating the product, and further, if desired, hydrolysing and, if necessary and desired, decarboxylating the alkylation product, and, if desired, esterifying the hydrolysed product. The compounds wherein n is 0 or 1 and R1 is C1-4 alkyl can also be prepared by reacting esters of the general formulae <FORM:0879576/IV (b)/4> with nitroalkanes of the general formula R4-CH2-NO2 to form compounds of the general formulae <FORM:0879576/IV (b)/5> and subjecting these to catalytic hydrogenation and the products to reductive alklyation if desired. The compounds in which R1 and R2 are both hydrogen can also be prepared by treating compounds of the general formula <FORM:0879576/IV (b)/6> with an alkali metal hypohalite, and, if desired, reductively alkylating the products. The compounds in which R1 is hydrogen can also be prepared by reacting compounds of the general formula <FORM:0879576/IV (b)/7> with compounds of the general formula <FORM:0879576/IV (b)/8> (wherein Am represents an imido group or an imido group which may be N-substituted by a C1-4 alkyl radical) in the presence of an alkaline condensing agent, and hydrolysing and, if desired, alkylating the product. The products are useful as fast acting central nervous system stimulants. Phenylacetic acid esters of the general formula <FORM:0879576/IV (b)/9> wherein R12 represents the COOR11 radical, and R11, R5 and n have the above significance are prepared, for example, by alkylating phenyl malonic acid diethyl esters with o -chloroalkyl cyanides. In examples diethyl phenyl malonate and chloracetonitrile and a -chloropropionitrile are reacted to form ethyl 2-carbethoxy-3-cyano-2-phenyl-propionate and -butyrate respectively. 3-Oximino-2-phenylbutyronitrile is prepared by reacting a -phenyl-acetoacetonitrile and hydroxylamine hydrochloride. Ethyl 2-(p-methoxyphenyl)-cyanoacetate is prepared by reacting diethyl carbonate and p-methoxyphenyl-acetonitrile in the presence of sodium. Ethyl a -phenyla -propyl-cyanoacetate is prepared by reacting diethyl carbonate and a -phenylvaleronitrile in the presence of sodium.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US879576XA | 1957-08-28 | 1957-08-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB879576A true GB879576A (en) | 1961-10-11 |
Family
ID=22208267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27567/58A Expired GB879576A (en) | 1957-08-28 | 1958-08-28 | Improvements in and relating to alkanoic acids and salts thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB879576A (en) |
-
1958
- 1958-08-28 GB GB27567/58A patent/GB879576A/en not_active Expired
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