Methanol → 7-(hydroxymethyl)thieno[3,2-c]quinolin-4(5H)-one

HRID 604365Notes

Reaction equation

HRID 604365 reaction equation
[O:1]=[C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15](O)=[O:16])=[CH:5][C:4]=2[NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.CO>O1CCOCC1.C(Cl)Cl>[OH:16][CH2:15][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[S:14][CH:13]=[CH:12][C:11]=3[C:2](=[O:1])[NH:3][C:4]=2[CH:5]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 509417534-Oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acid

Product 1

HCID 509417547-(hydroxymethyl)thieno[3,2-c]quinolin-4(5H)-oneYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylic acid (1.0 eq, 38 mg, 0.155 mmol) was suspended in dioxane (1 ml). LiAlH4 (7.0 eq, 40 mg, 1.05 mmol) was added and the mixture stirred at 100° C. for 45 nm. Water was added, then MeOH and CH2Cl2. The solid salts were filtered off and washed with MeOH and CH2Cl2. After evaporation of the volatiles in vacuo, the material was dissolved in a mixture of NMP, MeOH and water and was purified by preparative HPLC. Genevac evaporation afforded 7-(hydroxymethyl)thieno[3,2-c]quinolin-4(5H)-one as an off-white solid (12 mg, 34%). LCMS (ES): 95% pure, m/z 232 [M+1]+; 1H NMR (DMSO-d6, 400 MHz) δ 4.56 (s, 2H), 7.15 (d, J=7.6, 1H), 7.39 (br s, 1H), 7.55 (d, J=5.2, 1H), 7.73 (d, J=5.2, 1H), 7.76 (d, J=8.0, 1H), 11.73 (s, 1H) ppm.

Workup

  1. filtrationThe solid salts were filtered off
  2. washwashed with MeOH and CH2Cl2
  3. customAfter evaporation of the volatiles in vacuo
  4. dissolutionthe material was dissolved in a mixture of NMP, MeOH and water
  5. customwas purified by preparative HPLC
  6. customGenevac evaporation

Sources & evidence

ORD record
ord-2c270ef7f62c49699c9d3ed9dfcd9e86
Source dataset
uspto-grants-2011_03
Patent number
US07910600B2

Reaction notes

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