Hydrochloric Acid → 2-(Phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid

HRID 369966Notes

Reaction equation

HRID 369966 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].Cl>O>[C:25]1([CH2:24][O:23][C:21]([N:10]2[CH2:9][CH2:8][C:7]3[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH:11]2[CH2:14][C:15]([OH:17])=[O:16])=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14797Potassium HydroxideHCID 215842657-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid

Product 1

HCID 215843362-(Phenylmethoxy)carbonyl-7-nitro-1,2,3,4-tetrahydroisoquinolin-1-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline-1-acetic acid (5.0 g, 21.0 mmols) [Example 6(a)] in water (250 ml) at 0° C. was added 2M potassium hydroxide solution (15 ml). To this cooled solution was added in portions benzyl chloroformate (5.0 ml, 35 mmol) and the reaction mixture was stirred at 0° C. for 0.5 h. The solution was acidified with dilute hydrochloric acid and the precipitate which formed was collected. The dried solid was triturated with ether (200 ml) to give, after filtration, the title compound as a tan solid (4.83 g, 62%), m.p. 159.5-62° C.

Workup

  1. customthe precipitate which formed
  2. customwas collected
  3. customThe dried solid was triturated with ether (200 ml)
  4. customto give
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-052f47719e954de4856049636630f581
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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