Hydrochloric Acid → HCID 53664144, compound

HRID 1721510Notes

Reaction equation

HRID 1721510 reaction equation
[OH:1][C:2]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[N:5][C@@H:6]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH3:7].[BH4-].[Na+].Cl>C(O)C>[OH:1][C:2]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][C@@H:6]([C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 136378383HCID 136378383, compound

Product 1

HCID 53664144HCID 53664144, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.5 g (0.0283 mole) of (R)-(-)-N-(2-hydroxy-3-methoxybenzylidene)-1-(p-nitrophenyl)ethylamine were dissolved in 150 ml of ethyl alcohol. Then, 0.54 g (0.0143 mole) of sodium borohydride was added at room temperature to the reaction mixture, which was thereafter stirred at a temperature of from 30° to 35° C. for 2 hours, and then stirred at a temperature of from 55° to 60° C. for 2 hours. After the completion of the reaction, the reaction mixture was admixed with 30 ml of a 10% hydrochloric acid, and then concentrated under reduced pressure. The resulting residue was dissolved in 150 ml of water, washed with 100 ml of toluene, and separated into individual layers. The aqueous layer was neutralized or weakly alkalized with a 20% aqueous sodium hydroxide solution, and extracted twice with 100 ml of toluene. The toluene layer was washed with water, and concentrated under reduced pressure to give 7.75 g of (R)-(+)-N-(2-hydroxy-3-methoxybenzyl)-1-(p-nitrophenyl)ethylamine as crystalline substance. Yield: 90.6%. m.p. 112.5°-113.56° C.; a!D24 +64.0° (C 1.0, CHCl3) NMR-spectral data (δ ppm, CDCl3) 1.46 (d) 3H; 3.5-4.2 (m) 3H; 3.9 (s) 3H; 5.0-6.4 (broad) 1H; 6.4-6.9 (m) 3H 7.35-8.4 (m) 4H (s)

Workup

  1. stirringstirred at a temperature of from 55° to 60° C. for 2 hours
  2. customAfter the completion of the reaction
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in 150 ml of water
  5. washwashed with 100 ml of toluene
  6. customseparated into individual layers
  7. extractionextracted twice with 100 ml of toluene
  8. washThe toluene layer was washed with water
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42283fcef80d4967b2784c094ec14e32
Source dataset
uspto-grants-1996_04
Patent number
US05510519

Reaction notes

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