Malonic Acid → 7-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

HRID 369938Notes

Reaction equation

HRID 369938 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17]>C(O)(=O)C.C(O)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 37512877-Nitro-3,4-dihydroisoquinoline

Product 1

HCID 215842657-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 7-nitro-3,4-dihydroisoquinoline (10.0 g, 56.1 mmol) and malonic acid (11.7 g, 112 mmol) in acetic acid (55 ml) was heated at 120° C. for 0.5 h. Upon cooling, the solvent was concentrated to give a red oil which was taken up in aqueous ethanol (50 ml of 75%). After crystallization had occurred, the solvent was cooled to 0° C. and the product collected. The title compound was isolated as a tan solid (10.9 g, 81%), m.p. 264-5° C. (dec.).

Workup

  1. temperatureUpon cooling
  2. concentrationthe solvent was concentrated
  3. customto give a red oil which
  4. customAfter crystallization
  5. temperaturethe solvent was cooled to 0° C.
  6. customthe product collected

Sources & evidence

ORD record
ord-3eae7159982e4116a755149ee00ab8bc
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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