Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1) → HCID 14699557, compound

HRID 1608286Notes

Reaction equation

HRID 1608286 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.Cl.[NH:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])N>COC(C)(C)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[CH:3]=[N:2][N:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 545713423-(Dimethylamino)-2-(4-fluorophenyl)-1-phenylprop-2-en-1-one

Product 1

HCID 14699557HCID 14699557, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Following the procedure of example 1B, 13.8 g (0.0645 mol) of 2-(4-fluorophenyl)-1-phenylethanone was reacted with 20 mL of dimethyl formamide dimethyl acetal to yield 13.6 g of 3-(dimethylamino)-2-(4-fluorophenyl)-1-phenyl-2-propen-1-one, mp 115°-116° from isopropyl acetate. The enamine (10.5 g, 0.039 mol) was reacted with 6.03 g (0.039 mol) of ethyl hydrazinoacetate hydrochloride to yield 12.1 g of product mp 86°-87° C. from methyl-t-butyl ether.

Sources & evidence

ORD record
ord-3ce7e54b63924f07a71a0509aaeb5373
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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