Hydrochloric Acid → HCID 50941758, compound

HRID 2174910Notes

Reaction equation

HRID 2174910 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, δ: 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-d07672240afb4a529726af9b432ef7a6
Source dataset
uspto-grants-2015_06
Patent number
US09062043B2

Reaction notes

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