Hydroxylamine → 6-Amino-9-[(3-chlorophenyl)methyl]pyrido[3,4-b]indole-3-carbohydroxamic acid

HRID 891022Notes

Reaction equation

HRID 891022 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[C:10]1[CH:9]=[N:8][C:7]([C:23](OCC)=[O:24])=[CH:6][C:5]2=1.[OH-:28].[Na+].[NH2:30]O>CO.O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[C:10]1[CH:9]=[N:8][C:7]([C:23]([NH:30][OH:28])=[O:24])=[CH:6][C:5]2=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 21883389Ethyl 6-amino-9-(3-chlorobenzyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 30134666-Amino-9-[(3-chlorophenyl)methyl]pyrido[3,4-b]indole-3-carbohydroxamic acidYield 27%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 6-amino-9-(3-chlorobenzyl)-9H-β-carboline-3-carboxylate (139 mg, 0.37 mmol) in methanol (15 mL) under a nitrogen atmosphere were added NaOH (2N, 0.7 mL) and H2NOH (15 mL, 50 wt. % solution in H2O, 0.23 mol). The suspension was stirred for 7 days at ambient temperature and then diluted with H2O (10 mL). The mixture was filtered, and the solid was boiled in methanol (20 mL). After filtration, the title compound (36 mg, 27%) was obtained. 1H NMR (400 MHz, DMSO-d6): δ 11.17 (1H, s), 8.90–8.95 (2H, m), 8.55 (1H, s), 6.96–7.51 (7H, m), 5.72 (2H, s), 5.03 (2H, br, s). HRMS (M+H)+ found: 367.0961. Calcd for C19H16ClN4O2: 367.0962.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationAfter filtration

Sources & evidence

ORD record
ord-be4bbbe843e74f61baa2efdec36853e4
Source dataset
uspto-grants-2006_02
Patent number
US07001912B2

Reaction notes

Loading…