Hydrochloric Acid → HCID 19959717, compound

HRID 1461848Notes

Reaction equation

HRID 1461848 reaction equation
C([N:8]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:25])[CH:19]=2)[C:15]2[C:10](=[C:11]([NH:27][CH:28]=[O:29])[C:12]([OH:26])=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.[ClH:30]>C(O)C>[ClH:30].[OH:25][C:20]1[CH:19]=[C:18]([CH:16]2[C:15]3[C:10](=[C:11]([NH:27][CH:28]=[O:29])[C:12]([OH:26])=[CH:13][CH:14]=3)[CH2:9][NH:8][CH2:17]2)[CH:23]=[CH:22][C:21]=1[OH:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 199597152-Benzyl-4-(3,4-dihydroxyphenyl)-8-formamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 19959717HCID 19959717, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.25 ml of formic acid in 10 ml of chloroform, was added under ice cooling 0.88 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and then after 15 minutes, was added dropwise 5 ml of a solution of 8-amino-2-benzyl-4-(3,4-dihydroxyphenyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (0.88 g) in dimethylformamide. The temperature of the reaction mixture was reverted to room temperature, and the reaction was performed for further 30 minutes. The reaction mixture was concentrated, and the residue obtained was changed to precipitates by addition of standard buffer solution (×5). The precipitates were collected by filtration, and washed perfectly with water, affording 450 mg of 2-benzyl-4-(3,4-dihydroxyphenyl)-8-formylamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline. (3) 450 mg of 2-benzyl-4-(3,4-dihydroxyphenyl)-8-formamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline was dissolved in 9 ml of ethanol, and after adding thereto 0.86 ml of 2N hydrochloric acid 0.05 g of 10% paradium-carbon, hydrogenation reaction was performed at room temperature. The hydrogenation reaction was over, the reaction mixture was filtered, and concentrated. The residue was changed to precipitates with treatment of isopropyl alcohol and acetonitrile, and the precipitates was collected by filtration, affording 320 mg of 4-(3,4-dihyroxyphenyl)-8-formamido-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride.

Workup

  1. additionafter adding
  2. customwas performed at room temperature
  3. customThe hydrogenation reaction
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customto precipitates with treatment of isopropyl alcohol and acetonitrile
  7. filtrationthe precipitates was collected by filtration

Sources & evidence

ORD record
ord-ac68d6eb9dcb474f8d3f2fb45cd4f4c0
Source dataset
uspto-grants-1991_12
Patent number
US05077406

Reaction notes

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