Hydrochloric Acid → 7-Amino-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester dihydrochloride

HRID 583242Notes

Reaction equation

HRID 583242 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:19])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=2)[CH2:9][CH2:8][NH:7]1.CO.Cl>C(O)(C)C>[ClH:1].[ClH:1].[CH3:2][O:3][C:4](=[O:19])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=2)[CH2:9][CH2:8][NH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 701156367-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester hydrochloride

Product 1

HCID 701152177-Amino-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester dihydrochlorideYield 197.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid methyl ester hydrochloride (3.08 g, 10.7 mmol) in a solution of methanol (170 ml) and saturated hydrogen chloride in isopropanol (12 ml) was added 10% Pd--C (0.5 g). The reaction mixture was hydrogenated on a Parr Hydrogenator for 2 h at 50 psi. After the catalyst was removed by filtration, the solvent was concentrated to about 1/5 the volume. Isopropanol (70 ml) was added and the precipitate was collected to afford the title compound as a pale yellow solid (3.10 g, 98%), m.p. 245-6° C. (dec.).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe solvent was concentrated to about 1/5 the volume
  3. additionIsopropanol (70 ml) was added
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-f0dc8ec0322244438d39c6c09ea5f230
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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