4-Hydroxybenzaldehyde → HCID 3609106, compound

HRID 2379736Notes

Reaction equation

HRID 2379736 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[OH:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C.C(O)C>[CH2:1]([NH:4][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([OH:5])=[CH:7][CH:8]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 7852PropylamineHCID 4311764Sodium borohydride

Product 1

HCID 3609106HCID 3609106, compoundYield 130.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Propylamine (4.13 g) was slowly added to 4-hydroxybenzaldehyde (11.2 g, 91.80 mmol) in 50 mL of isopropanol at ambient temperature. The reaction was stirred for 1 hour and then cooled in an ice bath to 0° C. The imine was then reduced with sodium borohydride (1.74 g, 46 mmol) for 1 hour. The reaction was diluted with 100 mL of ethanol and acidified with acetic acid. The resulting solid was filtered and recrystallized from ethanol/isopropanol to give 15.1 g (99%) of the title compound. TLC (3:1 ethyl acetate/ethanol, trace triethylamine) Rf =0.37.

Workup

  1. filtrationThe resulting solid was filtered
  2. customrecrystallized from ethanol/isopropanol

Sources & evidence

ORD record
ord-b5f99abf6c084b7e8baacd6484eaf5ba
Source dataset
uspto-grants-1994_11
Patent number
US05364869

Reaction notes

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