Triethylamine → HCID 178454474, compound

HRID 1168805Notes

Reaction equation

HRID 1168805 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][C:16]([CH3:21])=[CH:15][CH:14]=2.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25]>ClCCl.C(=O)(O)[O-].[Na+]>[OH2:20].[C:22]([NH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][C:16]([CH3:21])=[CH:15][CH:14]=2)(=[O:26])[CH2:23][CH2:24][CH3:25].[C:22]([NH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][C:16]([CH3:21])=[CH:15][CH:14]=2)(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178423387HCID 178423387, compound

Product 1

HCID 178454474HCID 178454474, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Triethylamine (11.46 mL) was added to a suspension of 3-amino-6-methylquinolin-4-ol hydrochloride in dichloromethane (400 mL). Butyryl chloride (4.46 mL) was added. The reaction mixture was heated on a steam bath for 30 minutes. The solution was diluted with sodium bicarbonate and then filtered. The filtrate was washed with bicarbonate and then concentrated under vacuum. The residue was recrystallized from isopropanol to provide 3-butyramido-6-methylquinolin-4-ol hemihydrate as a solid, m.p. 274-277° C. Analysis: Calculated for C14H16N2O2½H2O: %C, 66.39; %H, 6.76; %N, 11.06; Found: %C, 66.56; %H, 6.46; %N, 11.03.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 30 minutes
  2. filtrationfiltered
  3. washThe filtrate was washed with bicarbonate
  4. concentrationconcentrated under vacuum
  5. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-a68f37d32f974882acce9719bd6e17fb
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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