Ammonia methanol → HCID 67264267, compound

HRID 1687946Notes

Reaction equation

HRID 1687946 reaction equation
[CH3:1][O:2][C:3]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:6]2[NH:7][C:8](=[O:18])[CH2:9][N:10](C(=O)C(F)(F)F)[CH2:11][C:5]=2[CH:4]=1.N.CO>CO>[CH3:1][O:2][C:3]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:6]2[NH:7][C:8](=[O:18])[CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 86633914HCID 86633914, compound

Product 1

HCID 67264267HCID 67264267, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-methoxy-8-nitro-4-(2,2,2-trifluoro-acetyl)-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (1.10 g, 3.3 mmol) in methanol (10 mL) cooled in an ice-water bath was added 7M NH3/MeOH (10 mL, 70 mmol). The mixture was stirred while being allowed to warm slowly to room temperature over 1.5 hours, concentrated on a rotary evaporator, and purified by flash chromatography over silica gel (0-20% MeOH/DCM) to afford 7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.75 g, 96%) as a yellow solid; NMR (400 MHz, DMSO-d6) δ 9.90 (s, 1H), 7.68 (s, 1H), 7.20 (s, 1H), 3.97 (s, 2H), 3.88 (3H), 3.51 (s, 2H); MS (m/e) 238 (M+1); mp 203° C. (dec.).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. custompurified by flash chromatography over silica gel (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-1d9c571acfd74f708fed8281c972d404
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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