Triethylamine → HCID 178460085, compound

HRID 913356Notes

Reaction equation

HRID 913356 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][CH:9]=[C:8]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:7]=2.C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>ClCCl>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([OH:13])=[C:3]([NH:2][C:29](=[O:32])[CH2:30][CH3:31])[CH:4]=[N:5]2)=[CH:10][CH:9]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178479098HCID 178479098, compound

Product 1

HCID 178460085HCID 178460085, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-amino-7-benzyloxyquinolin-4-ol hydrochloride (40.4 g, 133.4 mmol), and triethylamine (2.5 eq., 33.8 g, 333.6 mmol) in dichloromethane (1000 mL) at room temperature, was slowly added propionyl chloride (1.1 eq., 13.6 g, 146.8 mmol). After 6 hours the reaction was quenched with water (250 ml). The reaction mixture was transferred to a separatory funnel and the layers were separated. The dichloromethane layer was concentrated to provide 41.5 g of N-(7-benzyloxy-4-hydroxyquinolin-3-yl)propionamide as a pale tan crystalline solid. MS (ACPI) m/z=323 (M+H)+. This material was carried on without further purification to the next step.

Workup

  1. customat room temperature
  2. customAfter 6 hours the reaction was quenched with water (250 ml)
  3. customThe reaction mixture was transferred to a separatory funnel
  4. customthe layers were separated
  5. concentrationThe dichloromethane layer was concentrated

Sources & evidence

ORD record
ord-f507ba28dd02445abebcb8be8ede0567
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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