Water → 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

HRID 503825Notes

Reaction equation

HRID 503825 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.[OH-].[Na+].O>CC(N(C)C)=O.C1CCCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 14798Sodium Hydroxide2×HCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 105420647-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 31374DimethylacetamideSolvent

Procedure

1,4-dibromo butane (509 ml) was added to a stirred solution of 7-hydroxy-3,4-dihydrocarbostyril (100 gm) in dimethylacetamide (500 ml) at ambient temperature. The reaction mixture was heated at 36° to 40° C. Sodium hydroxide (33.1 gm) was added to the reaction mixture at the interval of 30 min (Complete the addition of sodium hydroxide in 9 equal fractions in 4.0 hours). The reaction mixture was cooled at ambient temperature and D.M Water was added to it. The reaction mixture was extracted with ethylacetate. Organic layer was separated and washed with 5% brine and finally dried over sodium sulphate. The organic layer was evaporated to dryness under reduced pressure (10 mm) at 45° C. to obtain residue. To the residue cyclohexane (1000 ml) was added to give of 7-(4-bromobutoxy)-3,4-dihydrocarbostyril.

Workup

  1. temperatureThe reaction mixture was heated at 36° to 40° C
  2. extractionThe reaction mixture was extracted with ethylacetate
  3. customOrganic layer was separated
  4. washwashed with 5% brine
  5. dry with materialfinally dried over sodium sulphate
  6. customThe organic layer was evaporated to dryness under reduced pressure (10 mm) at 45° C.
  7. customto obtain residue

Sources & evidence

ORD record
ord-a2ac5476bbdb4390a7c999ce2e318aa0
Source dataset
uspto-grants-2010_08
Patent number
US07777039B2

Reaction notes

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