GB903639A - Process for the production of 3-methyl-5-amino-pyrazole and the resulting product - Google Patents
Process for the production of 3-methyl-5-amino-pyrazole and the resulting productInfo
- Publication number
- GB903639A GB903639A GB30048/59A GB3004859A GB903639A GB 903639 A GB903639 A GB 903639A GB 30048/59 A GB30048/59 A GB 30048/59A GB 3004859 A GB3004859 A GB 3004859A GB 903639 A GB903639 A GB 903639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- carboxylic acid
- acid ester
- amino
- pyrazole
- 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
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003513 alkali Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000003518 caustics Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 abstract 1
- ZTDMWWJZGQVDAA-UHFFFAOYSA-N 5-amino-3-methylpyrazole-1-carboxylic acid Chemical compound CC=1C=C(N)N(C(O)=O)N=1 ZTDMWWJZGQVDAA-UHFFFAOYSA-N 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
3-Methyl-5-amino-pyrazole is prepared by reacting a compound of the formula CH3.(:X).CH2CN (wherein X represents oxygen or an amino group) with a hydrazine carboxylic acid ester to form a cyanoacetone hydrazone-N-carboxylic acid ester of the formula ROOC.NH-N:C(CH3).CH2CN (where R is, for example, methyl, ethyl, propyl, benzyl or phenyl) and either treating the latter with caustic alkalies (e.g. alkali metal or alkaline earth metal hydroxides) to effect ring closure, saponification of the carboxylic acid ester group and decarboxylation, or treating the hydrazone with mild alkalies (e.g. alkali metal carbonates) to effect ring closure to form 3-methyl - 5-aminopyrazole - 1-carboxylic acid ester and saponifying and decarboxylating this latter compound with caustic alkalies.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6358258A CH366547A (en) | 1958-09-04 | 1958-09-04 | Process for the preparation of 3-alkyl-5-aminopyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB903639A true GB903639A (en) | 1962-08-15 |
Family
ID=4525092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30048/59A Expired GB903639A (en) | 1958-09-04 | 1959-09-03 | Process for the production of 3-methyl-5-amino-pyrazole and the resulting product |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE582293A (en) |
| CH (1) | CH366547A (en) |
| GB (1) | GB903639A (en) |
-
1958
- 1958-09-04 CH CH6358258A patent/CH366547A/en unknown
-
1959
- 1959-09-03 GB GB30048/59A patent/GB903639A/en not_active Expired
- 1959-09-03 BE BE582293A patent/BE582293A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE582293A (en) | 1960-03-03 |
| CH366547A (en) | 1963-01-15 |
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