Hydrochloric Acid → 2-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acid

HRID 2174905Notes

Reaction equation

HRID 2174905 reaction equation
[Br:1][C:2]1[S:14][C:13]2[C:12]3[CH:11]=[CH:10][C:9]([C:15]([O:17]C)=[O:16])=[CH:8][C:7]=3[NH:6][C:5](=[O:19])[C:4]=2[CH:3]=1.CO.C1COCC1.O.[Li+].[OH-].Cl>O>[Br:1][C:2]1[S:14][C:13]2[C:12]3[CH:11]=[CH:10][C:9]([C:15]([OH:17])=[O:16])=[CH:8][C:7]=3[NH:6][C:5](=[O:19])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 57500654Methyl 2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate

Product 1

HCID 575006552-Bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acidYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate (1.0 eq, 17 mg, 0.050 mmol) was suspended in a 1:1:1 mixture of MeOH/THF/water (0.6 ml). LiOH (39 mg) was added and the mixture stirred at room temperature for one hour. Water and 6N HCl was added and the resulting precipitate was filtered. The material was purified by preparative HPLC. Genevac evaporation provided 2-bromo-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acid as a solid (2.1 mg, 13% yield). LCMS (ES): >95% pure, m/z 324 [M]+, 326[M+2]+; 1H NMR (DMSO-d6, 400 MHz) δ 7.75 (s, 1H), 7.75 (dd, J=1.6, J=8.0, 1H), 7.90 (d, J=8.4, 1H), 8.03 (d, J=1.6, 1H), 12.06 (s, 1H) ppm.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customThe material was purified by preparative HPLC
  3. customGenevac evaporation

Sources & evidence

ORD record
ord-48ce46b7b9ab4c55acd2e074ba8afea0
Source dataset
uspto-grants-2015_06
Patent number
US09062043B2

Reaction notes

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