Water → 6-Bromo-4-methylquinolin-2-ol

HRID 279994Notes

Reaction equation

HRID 279994 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.O>C(OCC)(=O)C>[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

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 598820N-(4-Bromophenyl)-3-oxobutanamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.00 g (0.0117 moles) of N-(4-bromophenyl)-3-oxobutyramide and 6 ml concentrated sulfuric acid was stirred and heated to 95°-100° C. (H2O bath) for 11/2 hours. The resulting solution was poured onto an ice/H2O mixture to yield a white crystalline product. The crystals were collected and taken up in 200 ml absolute ethanol. The volume was reduced to 150 ml followed by chilling; crystals were isolated (0.71 g 25.6%), mp 292°-299° C. Anal. Calcd. for C10H8BrNO: C, 50.45; H, 3.39; N, 5.88; Br, 33.56. Found: C, 50.28; H, 3.44; N, 5.83; Br, 33.68. A TLC of the product on silica showed Rf 0.18 with ethyl acetate eluent.

Workup

  1. customto yield a white crystalline product
  2. customThe crystals were collected
  3. temperatureby chilling
  4. customcrystals were isolated (0.71 g 25.6%), mp 292°-299° C

Sources & evidence

ORD record
ord-799faa5126984ad4bbfb1576df919f62
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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