Sulfuric Acid → HCID 20454432, compound

HRID 1461979Notes

Reaction equation

HRID 1461979 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]1[C:16]([Cl:21])=[CH:17][C:18]([Cl:20])=[CH:19][N:10]1[C:9]2=[O:22])[CH3:5].S(=O)(=O)(O)O.[OH-].[Na+]>O>[Cl:21][C:16]1[C:11]2=[N:12][C:13]3[C:8]([C:9](=[O:22])[N:10]2[CH:19]=[C:18]([Cl:20])[CH:17]=1)=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:23])=[O:2])=[CH:15][CH:14]=3

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 56618376HCID 56618376, compound

Product 1

HCID 20454432HCID 20454432, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.4 g. of 2-(6,8-dichloro-11-oxo-11H-pyrido[2,1-b]quinazolin-2-yl)propionic acid methyl ester, 10 ml. of water, and 10 ml. of concentrated sulfuric acid is stirred for 4 hours at 120° (bath temperature). After cooling, the mixture is diluted with 10 ml. of ice water and adjusted with sodium hydroxide solution to a pH of 4-5. After extraction with ethyl acetate, drying, and concentration of the organic phase, 1.1 g. of 2-(6,8-dichloro-11-oxo-11H-pyrido[2,1-b]quinazolin-2-yl)propionic acid is obtained, m.p. 241° (dimethylformamide-water).

Workup

  1. additionA mixture of 1.4 g
  2. temperatureAfter cooling
  3. additionthe mixture is diluted with 10 ml
  4. extractionAfter extraction with ethyl acetate
  5. customdrying

Sources & evidence

ORD record
ord-9985467e28df45ac8afcc30a5ce907bc
Source dataset
uspto-grants-1984_07
Patent number
US04457927

Reaction notes

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