Hydrazine → 7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid hydrazide

HRID 2427511Notes

Reaction equation

HRID 2427511 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[C:10](=[O:15])[N:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:8]2)=O.[NH2:28][NH2:29]>C(O)C>[CH3:14][C:12]1[CH:13]=[C:5]([C:3]([NH:28][NH2:29])=[O:2])[CH:6]=[C:7]2[C:11]=1[C:10](=[O:15])[N:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 579494347-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester

Product 1

HCID 579496127-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester (190.0 mg, 0.5 mmol) was mixed with hydrazine (in water) 125.0 mg, 2.50 mmol) in ethanol (0.5 mL) and the reaction was refluxed for five hours. The reaction was concentrated to provide the title compound as an off white solid (200.0 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 7.63 (s, 1H), 7.54 (broad s, 1H), 7.31 (m, 2H), 7.18 (d, 2H), 4.75 (s, 2H), 4.22 (s, 2H), 2.74 (s, 3H).

Workup

  1. temperaturethe reaction was refluxed for five hours
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-f8867d5cc5224b1da05b4a6773e2146b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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