Formic Acid → 3-Benzyloxy-6-formylaminomethyl-2-methylpyridine

HRID 2417829Notes

Reaction equation

HRID 2417829 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[CH:18](O)=[O:19]>>[CH2:11]([O:10][C:6]1[C:7]([CH3:9])=[N:8][C:3]([CH2:2][NH:1][CH:18]=[O:19])=[CH:4][CH:5]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 233218896-Aminomethyl-3-benzyloxy-2-methylpyridine

Product 1

HCID 133736373-Benzyloxy-6-formylaminomethyl-2-methylpyridine

Procedure

A solution of 6-aminomethyl-3-benzyloxy-2-methylpyridine (6.31 g) in 8.7 ml of formic acid is heated at 90° for 15 hours. The reaction mixture is cooled, made basic with ice-cold ammonium hydroxide solution and extracted with chloroform. (3×25 ml). The chloroform extract is dried over sodium sulfate and evaporated. Recrystallization from ether yields 3-benzyloxy-6-formylaminomethyl-2-methylpyridine, m.p. 67°-68°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialis dried over sodium sulfate
  5. customevaporated
  6. customRecrystallization from ether

Sources & evidence

ORD record
ord-9e10afa67fbe40fa82cb0b744d2ac28a
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

Loading…