HCID 21584384, compound → HCID 21584269, compound

HRID 369991Notes

Reaction equation

HRID 369991 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([N+:13]([O-])=O)=[CH:8][CH:9]=2)[CH:4]1[CH2:16][CH2:17][CH3:18]>C(O)C>[ClH:1].[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([NH2:13])=[CH:8][CH:9]=2)[CH:4]1[CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 1

HCID 21584384HCID 21584384, compound

Product 1

HCID 21584269HCID 21584269, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-methyl-7-nitro-1-propyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.30 g, 4.80 mmol) in ethanol (100 ml) was added 10% Pd--C (0.2 g) and the reaction mixture was hydrogenated at 50 psi for 3 h. The solution was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in isopropanol (30 ml) and allowed to stand overnight to give the title compound (1.04 g, 90%) as a tan solid, m.p. 217-9° C. (dec.).

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in isopropanol (30 ml)
  4. waitto stand overnight

Sources & evidence

ORD record
ord-baf54bc3ce4544df9415f61f9173e628
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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