Hydroxylamine → HCID 178513288, compound

HRID 859610Notes

Reaction equation

HRID 859610 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:27]=[CH:26][C:11]3[N:12]=[C:13]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[NH2:28][OH:29]>CCO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:27]=[CH:26][C:11]3[N:12]=[C:13]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]([NH:28][OH:29])=[NH:22])[CH2:14][C:15](=[O:17])[NH:16][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 97987263-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile

Product 1

HCID 178513288HCID 178513288, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-benzonitrile (Example 57) (355 mg, 1 mmol) in EtOH (60 mL) was added at 23° C. over 6 h 50% aqueous hydroxylamine solution (3.48 mL, 60 mmol) in 6 portions. The mixture was cooled in the ice-bath, diluted with H2O (100 mL) and stirred for 1 h. The precipitate was collected by filtration, washed with water and Et2O, and triturated with ethyl acetate to give the title compound as light yellow solid (336 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and Et2O
  3. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-c6821316c05f4d7c86f1695c18a6ec61
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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