Dimethylformamide → 2-Aminoquinoline-6-carbaldehyde
Reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[CH:6]=[CH:5]2.C(N(CC)CC)C.C1(C(C2C=CC=CC=2)CCP)C=CC=CC=1.C([SiH](CCCCCC)CCCCCC)CCCCC.CN(C)[CH:57]=[O:58]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:57]=[O:58])[CH:3]=2)[N:8]=1Participants
Procedure
A mixture of 6-iodo-quinolin-2-ylamine (200 mg, 0.74 mmol), triethylamine (0.26 mL, 1.85 mmol), diphenylpropylphosphine (dpp, 17 uL, 0.074 mmol) and palladium(II) acetate (17 mg, 0.074 mmol) in dry N,N-dimethylformamide (4 mL) in pressure tube was stirred under carbon monoxide at 75 psi at room temperature for 10 min. After addition of trihexylsilane (0.53 mL, 1.5 mmol), the mixture was then stirred under carbon monoxide at 75 psi at 80° C. for 4 h. The reaction was allowed to cool to 25[ ]C and then extracted with methylene chloride (2×50 mL). The combined organic layers were successively washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, ethyl acetate) afforded 2-amino-quinoline-6-carbaldehyde (30 mg, 24%) as a solid.
Workup
- stirringthe mixture was then stirred under carbon monoxide at 75 psi at 80° C. for 4 h
- temperatureto cool to 25[ ]C
- extractionextracted with methylene chloride (2×50 mL)
- washThe combined organic layers were successively washed with water (3×50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7e0497d3457b4dd1916693b1caee48d4
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241893B2
Reaction notes
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