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

HRID 722127Notes

Reaction equation

HRID 722127 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-2968765aed734cf5809b9d2fa2b3a3a4
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Reaction notes

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