Phenylhydrazine → HCID 21327578, compound

HRID 615017Notes

Reaction equation

C1(C(=O)CC(C2C=CC=CC=2)=O)C=CC=CC=1.[H-].[Na+].C(OC(=O)C(Br)C)C.C([O:30][C:31](=[O:51])[CH:32]([CH3:50])[CH:33]([C:42](=O)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C.[C:52]1([NH:58][NH2:59])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C(O)(=O)C.CN(C)C=O>[CH3:50][CH:32]([C:33]1[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:59][N:58]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:34]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31]([OH:30])=[O:51]

Participants

Conditions

Temperature: 50 °C

Procedure

20 grams 1,3-diphenyl-1,3-propanedione, 4.3 grams of a 50% suspension of sodium hydride in paraffin oil, 20 grams α-bromopropionic acid-ethyl ester and 300 milliliters dimethylformamide were mixed and the mixture was stirred for 20 hours at room temperature and for another 20 hours at 50° C. The reaction mixture containing the 2-methyl-3,3-dibenzoyl-propionic acid-ethyl ester formed in the reaction was worked up in accordance with a procedure analogous to that set out in Example (2b). The crude product obtained thereby was further reacted with 9.0 grams phenylhydrazine and 8 grams glacial acetic acid in accordance with a procedure analogous to that described in Example (2c). The crude pyrazol ester obtained in this manner was saponified to form the free acid in a procedure analogous to that set above. 5.7 grams Methyl-1,3,5-triphenyl-pyrazol-4-acetic acid, melting at 95°-99° C. were obtained, corresponding to a yield of 17% based on the diketone starting material.

Workup

customformed in the reaction
customThe crude product obtained
customThe crude pyrazol ester obtained in this manner
customto form the free acid in a procedure analogous to

Sources & evidence

ORD record: ord-efb54c47df764f32a6efbf223711ee4c
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146721

Reaction notes

Loading…