Hydrazine → HCID 57654578, compound

HRID 1921646Notes

Reaction equation

HRID 1921646 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:8]2=[O:24].[NH2:26][NH2:27]>CO>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:9]2[C:8](=[O:24])[C:7]3[C:12](=[CH:13][CH:14]=[C:5]([CH2:4][C:3]([NH:26][NH2:27])=[O:2])[CH:6]=3)[N:11]=[CH:10]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57654610HCID 57654610, compound

Product 1

HCID 57654578HCID 57654578, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[3-(4-Methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid methyl ester (0.050 g, 0.148 mmol) and hydrazine (0.047 g, 0.148 mmol) were stirred at 50° C. in methanol (5 mL) for several hours. The reaction was then cooled to room temperature and filtered to give 0.030 g (60%) of [3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-acetic acid hydrazide. 1H NMR (400 MHz, CD3OD) δ 10.09 (s, 1H), 9.33 (s, 1H), 8.85 (m, 1H), 8.53 (d, 1H, J=2.0, 8.4 Hz), 8.42 (d, 1H, J=8.4 Hz), 8.14 (d, 2H, J=8.4 Hz), 7.70 (d, 2H, J=8.4 Hz), 5.93 (s, 2H), 5.04 (bs, 2H), 4.52 (s, 3H), 4.31 (s, 2H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-288477bc43b545048ea9733a4b27f1fc
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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