Acetic Acid → 2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[OH-].[Na+].C=O.[C:19](O)(=O)C.C([BH3-])#N.[Na+]>ClC(Cl)C>[CH3:19][N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Into a 125 mL Erlenmeyer flask was charged 7-nitro-1,2,3,4-tetrahydroisoquinoline, hydrochloric acid (3.17 g, 14.77 mmol) in dichloroethane (148 ml). The solution was stirred 10 minutes with 1 N NaOH, and the layers were separated. Paraformaldehyde (2.217 g, 73.8 mmol), acetic acid (4.23 ml, 73.8 mmol) and sodium cyanoborohydride (4.64 g, 73.8 mmol) were added. The reaction was heated at 90° C. overnight. The reaction was cooled to room temperature, and quenched with saturated aqueous sodium bicarbonate. The layers were separated, and the organic layer was dried over MgSO4, filtered, and concentrated onto silica gel. The reaction was purified by flash chromatography (50% ethyl acetate:hexanes for 20 minutes, then to 100% ethyl acetate:hexanes over 30 minutes) to provide the title compound. MS (DCI) m/e 193 (M+H)+.
Workup
- customthe layers were separated
- temperatureThe reaction was cooled to room temperature
- customquenched with saturated aqueous sodium bicarbonate
- customThe layers were separated
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated onto silica gel
- customThe reaction was purified by flash chromatography (50% ethyl acetate
Sources & evidence
- ORD record
- ord-1da90e482cf8465282d6c3e111777ac3
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354422B2
Reaction notes
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