Water → HCID 12899414, compound

HRID 621544Notes

Reaction equation

HRID 621544 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2)(=[O:3])[CH3:2].O.[Br:17]Br>C(O)(=O)C>[Br:17][C:12]1[CH:13]=[CH:14][C:5]([O:4][C:1](=[O:3])[CH3:2])=[C:6]2[C:11]=1[NH:10][C:9](=[O:15])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962Water2×HCID 24408BromineHCID 128994132-Oxo-1,2,3,4-tetrahydroquinolin-5-yl acetate

Product 1

HCID 12899414HCID 12899414, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

20.5 grams of 5-acetyloxy-3,4-dihydrocarbostyril are dissolved in 200 ml of acetic acid. This solution is stirred under cooling with water and 60 ml of acetic acid solution containing 16 g of bromine are added dropwise over 30 minutes and the reaction is carried out for 2 hours at the same temperature. The reaction mixture is poured into 300 ml of water and allowed to stand for 3 hours and the crystals thus precipitated are separated by filtration, and recrystallized from methanol to obtain 21 g of 8-bromo5-acetyloxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with a melting point of 237°-239° C.

Workup

  1. additionare added dropwise over 30 minutes
  2. waitto stand for 3 hours
  3. customthe crystals thus precipitated
  4. customare separated by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-56bf48cc962949c8b5490fefba53c3d1
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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