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

HRID 1919641Notes

Reaction equation

HRID 1919641 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-2090ed9bb0b543aba7a03117a0b336ed
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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