Sodium Hydroxide → 7-Bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

HRID 326622Notes

Reaction equation

HRID 326622 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[CH:14]=1)=[C:11]([CH3:16])[CH:10]=[C:9]([Br:17])[CH:8]=2)=[O:4].[OH-].[Na+].[CH]Cl>O>[Br:17][C:9]1[CH:8]=[C:7]2[C:12]([C:13](=[O:15])[CH:14]=[C:5]([C:3]([OH:4])=[O:2])[NH:6]2)=[C:11]([CH3:16])[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 19735190Methyl-7-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 148427357-Bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acidYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl-7-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.40 g) in water (10 ml) containing sodium hydroxide (0.22 g) was refluxed for 10 minutes, then acidified with cHCl. The precipitate was collected and recrystallised from H2O/EtOH/NaOH on addition of cHCl to give 7-bromo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (0.35 g), mp 299° C. (dec.). m/e 283, 281 (M+); δ (360 MHz, NaOD-D2O) 2.86 (3H, s, CH3), 6.85 (1H, s, 3-H), 7.22 (1H, d, 6-H) and 7.83 (1H. d, 8-H).

Workup

  1. temperaturewas refluxed for 10 minutes
  2. customThe precipitate was collected
  3. customrecrystallised from H2O/EtOH/NaOH on addition of cHCl

Sources & evidence

ORD record
ord-f286a0af9b354b05895fbea07056b85b
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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