Sodium Hydroxide → 6-Nitro-4-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

HRID 1157691Notes

Reaction equation

HRID 1157691 reaction equation
[CH3:1][N:2]([CH2:13][CH:14](OC)[O:15][CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>>[N+:10]([C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[CH2:3][N:2]([CH3:1])[CH2:13][CH:14]2[O:15][CH3:16])([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 68643690N-methyl-N-(4-nitrophenylmethyl)-2,2-dimethoxy-ethylamine

Product 1

HCID 686436866-Nitro-4-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline

Procedure

A mixture of 0.83 g of N-methyl-N-(4-nitrophenylmethyl)-2,2-dimethoxy-ethylamine and 3.0 ml trifluoromethanesulphonic acid is prepared in a dry ice/ethanol cooling bath, slowly brought to ambient temperature and stirred for 18 h. Then it is poured onto ice water, made alkaline with 2N NaOH, extracted 3× with EtOAc, the organic phases are dried with Na2SO4, concentrated and purified by repeated chromatography.

Workup

  1. customis prepared in a dry ice/ethanol cooling bath
  2. customslowly brought to ambient temperature
  3. additionThen it is poured onto ice water
  4. extractionextracted 3× with EtOAc
  5. dry with materialthe organic phases are dried with Na2SO4
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-481341cb27ac402e80b475eda0a7f8d9
Source dataset
uspto-grants-2010_10
Patent number
US07807693B2

Reaction notes

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