Acetic Acid → {2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([CH:19]=[O:20])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][OH:20])[N:10]=2)=[CH:4][CH:3]=1Participants
5
Procedure
2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbaldehyde (150 mg, 0.56 mmol) was dissolved in 5 mL dichloroethan. Acetic acid (136 mg, 2.3 mmol) and sodium triacetoxy borohydride (258 mg, 1.2 mmol) were added. The reaction mixture was stirred at room temperature overnight and quenched by addition of 2N sodium carbonate solution (50 mL). The mixture was extracted three times with ethyl acetate (100 mL each). The organic phases were pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a light brown solid (105 mg, 69%), MS: m/e=269.5 (M+H+).
Workup
- customquenched by addition of 2N sodium carbonate solution (50 mL)
- extractionThe mixture was extracted three times with ethyl acetate (100 mL each)
- dry with materialdried with sodium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->50:50 gradient)
Sources & evidence
- ORD record
- ord-e635a2a9f43f464a90b0ecf7c801b485
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989628B2
Reaction notes
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