Water → HCID 70542795, compound

HRID 1732402Notes

Reaction equation

HRID 1732402 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[NH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.O>C1C=CC=CC=1>[CH:1](=[C:12]1[CH:13]=[C:8]([CH2:7][NH2:6])[CH:9]=[CH:10][NH:11]1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6561IsobutyraldehydeHCID 773174-Pyridinemethanamine

Product 1

HCID 70542795HCID 70542795, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

227 g (3.15 mols) of isobutyraldehyde is added dropwise, within 1.5 hours, to a solution of 324 g (3.0 mols) of 4-aminomethylpyridine in 300 ml of benzene, the addition being made in a manner ensuring that the temperature in the solution does not exceed 35° C. The water which has formed (about 39 g) is separated, and the benzene (with residual water) is distilled off under a slight water-jet vacuum. The residue is distilled in an oil-pump vacuum. After a small preliminary fraction of 5 g, there is obtained 445 g (2.75 mols) of isobutylidene-4-aminomethylpyridine as a slightly yellowish main fraction, corresponding to a yield of 91.5% of theory; b.p. 81.5°-82° C./133 Pa; nD° =1.5105.

Workup

  1. additionthe addition
  2. customdoes not exceed 35° C
  3. customis separated
  4. distillationthe benzene (with residual water) is distilled off under a slight water-jet vacuum
  5. distillationThe residue is distilled in an oil-pump vacuum

Sources & evidence

ORD record
ord-be90c44a024f4bc3a70f50d9417a0142
Source dataset
uspto-grants-1980_12
Patent number
US04237275

Reaction notes

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