O-Methylhydroxylamine → HCID 72234593, compound

HRID 545578Notes

Reaction equation

HRID 545578 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][CH:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=O)[CH:11]=2.[O:30]([NH2:32])[CH3:31].[OH-].[Na+]>CCO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][CH:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=[N:32][O:30][CH3:31])[CH:11]=2

Participants

6

Reactant 3

HCID 4113O-MethylhydroxylamineHCID 14798Sodium Hydroxide2×HCID 59161203HCID 59161203, compound

Product 1

HCID 72234593HCID 72234593, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Combine cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Preparation 70) (0.32 g, 0.82 mmol), methoxylamine (0.21 g, 2.4 mmol), and sodium hydroxide (0.049 g, 1.3 mmol) in EtOH (15 mL). Add enough water to dissolve the sodium hydroxide and stir for 18 h. Dilute with water and extract with EtOAc. Dry EtOAc extracts over Na2SO4 and filter twice through a pad of silica to give 0.21 g (61%) of an off-white solid. MS (ES): m/z 420 (M+1).

Workup

  1. extractionextract with EtOAc
  2. filtrationfilter twice through a pad of silica

Sources & evidence

ORD record
ord-8ba5de69e0824ed6a328be858c7986a0
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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