Hydrochloric Acid → HCID 50941758, compound

HRID 1919646Notes

Reaction equation

HRID 1919646 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[S:19][CH:20]=[CH:21][C:7]=2[C:6]1=[O:22].[Li+].[OH-].Cl>C1COCC1.CO.O>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=[CH:10][C:9]=2[C:8]2[S:19][CH:20]=[CH:21][C:7]=2[C:6]1=[O:22]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 50941756HCID 50941756, compound

Product 1

HCID 50941758HCID 50941758, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-(3-hydroxypropyl)-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate (1.0 eq, 19 mg, 0.060 mmol) was dissolved in a 1:1:1 mixture of THF, MeOH and water (0.5 ml). LiOH (40 mg) was added and the resulting mixture stirred at room temperature for 1.5 hours. Water, MeOH and HCl were added and the solution purified by preparative HPLC. Genevac evaporation afforded 5-(3-hydroxypropyl)-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acid as a white solid (4 mg, 22% yield). LCMS (ES): 95% pure, m/z 304 [M+1]+. 1H NMR (CDCl3/CD3OD, 9:1, 400 MHz) δ 2.08 (qi, J=6.0, 2H), 3.61 (t, J=5.2, 2H), 4.62 (t, J=6.0, 2H), 7.53 (d, J=5.2, 1H), 7.77 (d, J=5.2, 1H), 7.93 (d, J=8.0, 1H), 7.99 (dd, J=1.2, J=8.4, 1H), 8.26 (d, J=0.8, 1H) ppm.

Workup

  1. customthe solution purified by preparative HPLC
  2. customGenevac evaporation

Sources & evidence

ORD record
ord-4b4bd41375f04fa496a12469bf7a9f93
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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