Dimethylformamide → Isoquinoline-4-carbaldehyde
Reaction equation
C([Li])CCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9][CH:8]=1.CN(C)[CH:19]=[O:20]>O1CCCC1>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH:19]=[O:20])=[CH:8][N:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium (1.6 M in hexanes, 11.0 ml, 17.6 mmol) is added dropwise to a stirred solution of 4-bromoisoquinoline (3.02 g, 14.5 mmol) and anhydrous tetrahydrofuran (100 ml) at −78° C. under nitrogen. The reaction is stirred for 45 min at −78° C. and then dimethylformamide (6.0 ml, 77.5 mmol) is added. The reaction is then stirred for 3 h at −78° C. before it is quenched with water. The reaction is then poured into saturated sodium bicarbonate solution (200 ml) and extracted with ethyl acetate (100 ml×3). The ethyl acetate is washed with brine and dried over sodium sulfate. The sodium sulfate is filtered and the crude product is concentrated on a rotary evaporator. The crude product is purified by flash chromatography on silica gel eluting with 50% ethyl acetate/hexanes to yield (0.74 g, 33%) of isoquinoline-4-carboxaldehyde: mass spectrum (ion spray): m/z=158.1 (M+1).
Workup
- stirringThe reaction is then stirred for 3 h at −78° C. before it
- customis quenched with water
- additionThe reaction is then poured into saturated sodium bicarbonate solution (200 ml)
- extractionextracted with ethyl acetate (100 ml×3)
- washThe ethyl acetate is washed with brine
- dry with materialdried over sodium sulfate
- filtrationThe sodium sulfate is filtered
- concentrationthe crude product is concentrated on a rotary evaporator
- customThe crude product is purified by flash chromatography on silica gel eluting with 50% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-3fb5f677dcb64dfc8f57a0ed668ef543
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07521462B2
Reaction notes
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