N-(4-Bromophenyl)-3-oxobutanamide → 6-Bromo-4-methylquinolin-2-ol

HRID 734781Notes

Reaction equation

HRID 734781 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[CH2:10][C:11](=O)[CH3:12])=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:9](=[O:14])[CH:10]=[C:11]2[CH3:12]

Participants

3

Reactant 1

HCID 598820N-(4-Bromophenyl)-3-oxobutanamide

Product 1

HCID 63244626-Bromo-4-methylquinolin-2-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 50.0 g (195 mmol) of N-(4-bromophenyl)-3-oxobutyramide in 217 mL of concentrated sulfuric acid was heated to 120° C. for 1 hour. After cooling to RT, the reaction solution was added to 1.5 L of ice water, stirred for 30 minutes, and the precipitate formed was filtered and washed with 4 L of water. Subsequently it was dried at 35° C. in the circulating air dryer until a constant weight was achieved. Yield: 24.0 g (52% of theoretical); C10H8BrNO (M=238.081); calc.: molpeak (M+H)+: 238/240 (Br); found: molpeak (M+H)+: 238/240 (Br); HPLC-MS: 4.8 minutes (method B).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. washwashed with 4 L of water
  4. customSubsequently it was dried at 35° C. in the circulating air dryer until a constant weight
  5. custom4.8 minutes (method B)

Sources & evidence

ORD record
ord-aa7c223930dc492fb158af6702b3fd28
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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