Hydrochloric Acid → HCID 70434271, compound

HRID 977968Notes

Reaction equation

HRID 977968 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:12].[CH3:13][O:14][C:15](=[O:19])[CH2:16][CH2:17][NH2:18].[BH4-].[Na+].Cl>CO.C(N(CC)CC)C>[ClH:12].[CH3:13][O:14][C:15](=[O:19])[CH2:16][CH2:17][NH:18][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 70434271HCID 70434271, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of p-nitrobenzaldehyde (1.51 g), β-alanine methyl ester hydrochloride (1.40 g), triethylamine (1.6 ml) and methanol (20 ml) is stirred at room temperature for 25 minutes. The mixture is ice-cooled, and sodium borohydride (807 mg) is added thereto. The mixture is stirred at the same temperature for 10 minutes. The mixture is acidified with 10% HCl, and extracted with ethyl acetate. The aqueous layer is neutralized with 10% NaOH, and extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent. The residue is dissolved in ether, and a HCl-ether solution is added thereto. The precipitates are collected and recrystallized from methanol to give N-(p-nitrobenzyl)-β-alanine methyl ester hydrochloride (1.95 g, 71.1%) as pale yellow plates, m.p. 219.5°-220° C. (decomp.).

Workup

  1. temperaturecooled
  2. stirringThe mixture is stirred at the same temperature for 10 minutes
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with a saturated sodium chloride solution
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. dissolutionThe residue is dissolved in ether
  10. additiona HCl-ether solution is added
  11. customThe precipitates are collected
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d2ad1debb64544c18804d75dad929627
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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