Hydrogen Bromide → 3-Quinolinecarboxylicacid,7-hydroxy-2-methyl-(6CI)

HRID 1748367Notes

Reaction equation

HRID 1748367 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]([OH:16])=[O:15])[C:9]([CH3:13])=[N:10]2)=[CH:5][CH:4]=1.Br>O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]([OH:16])=[O:15])[C:9]([CH3:13])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 8182487-methoxy-2-methylquinoline-3-carboxylic acid

Product 1

HCID 1362196283-Quinolinecarboxylicacid,7-hydroxy-2-methyl-(6CI)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 7-hydroxy-2-methylquinoline-3-carboxylate (V), where R3 is —CH3, is obtained in two steps from commercially available or synthetically accessible 7-methoxy-2-methylquinoline-3-carboxylic acid. Demethylation of 7-methoxy-2-methylquinoline-3-carboxylic acid, employing methods previously described, for example, HBr in H2O, at temperatures ranging from 80° C. to about 100° C., preferably ° C. for a period of 0.5 h to 24 h, preferably about 2 h provides 7-hydroxy-2-methylquinoline-3-carboxylic acid. Subsequent esterification of 7-hydroxy-2-methylquinoline-3-carboxylic acid employing methods previously described, provides ethyl 7-hydroxy-2-methylquinoline-3-carboxylate (V), where R3 is —CH3.

Workup

  1. customranging from 80° C. to about 100° C.
  2. waitfor a period of 0.5 h to 24 h

Sources & evidence

ORD record
ord-83070830b4374b31adcf5c958e240a39
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

Loading…