Pyridine → 9-Hydroxyimino-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide

HRID 1710456Notes

Reaction equation

HRID 1710456 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[C:15]4[C:22](=O)[CH2:21][CH2:20][CH2:19][N:16]43)=[CH:12][CH:11]=2)=[O:9])[CH:2]=1.Cl.[NH2:25][OH:26].N1C=CC=CC=1>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[C:15]4[C:22](=[N:25][OH:26])[CH2:21][CH2:20][CH2:19][N:16]43)=[CH:12][CH:11]=2)=[O:9])[CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 156048459-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide

Product 1

HCID 731995019-Hydroxyimino-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamideYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

9-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide (150 mg, 0.491 mmol), hydroxylamine hydrochloride (1.50 g, 21.6 mmol), and pyridine (3 mL) were combined in MeOH (40 mL) and heated to 60 □C for 20 h. The reaction was cooled and diluted with water (200 mL). The resulting precipitate was filtered, washed with water, then hexanes, and dried in a vacuum oven to give the title compound (122 mg, 78%) as an analytically pure mixture of oxime regioisomers (2:1).

Workup

  1. temperatureheated to 60 □C for 20 h
  2. temperatureThe reaction was cooled
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. dry with materialhexanes, and dried in a vacuum oven

Sources & evidence

ORD record
ord-b2c65f3e569d43a9bfdf2aa40f190e28
Source dataset
uspto-grants-2010_09
Patent number
US07790712B2

Reaction notes

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