Sodium Hydroxide → HCID 10377395, compound

HRID 1885187Notes

Reaction equation

HRID 1885187 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([O:17]C)=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([OH:17])=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10355418HCID 10355418, compound

Product 1

HCID 10377395HCID 10377395, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Butyryl-4-chloro-6-methoxyquinoline (7.9 g) was stirred in dry dichloromethane (150 ml) under nitrogen and boron tribromide (8.5 ml) was added via a syringe. The mixture was stirred overnight then cautiously added to a large volume of ice. The mixture was taken to pH 14 with sodium hydroxide solution, washed with dichloromethane, neutralized with hydrochloric acid and extracted several times with dichloromethane. The combined extracts were washed with brine, dried, filtered and evaporated to give 3-butyryl-4-chloro-6-hydroxyquinoline as a yellow powder (1.5 g, 20%) m.p. 157°-160°.

Workup

  1. additionthen cautiously added to a large volume of ice
  2. washwashed with dichloromethane
  3. extractionextracted several times with dichloromethane
  4. washThe combined extracts were washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b11c816391944bb4a80b5e79c39d0c82
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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