Ammonia → HCID 19771699, compound

HRID 1614587Notes

Reaction equation

HRID 1614587 reaction equation
[CH3:1][C:2]1O[C:6]2[CH2:8][CH2:9][O:10][CH2:11][C:5]=2[C:4](=[O:12])[CH:3]=1.[NH3:13]>>[CH3:1][C:2]1[NH:13][C:6]2[CH2:8][CH2:9][O:10][CH2:11][C:5]=2[C:4](=[O:12])[CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19771700HCID 19771700, compound

Product 1

HCID 19771699HCID 19771699, compound

Procedure

Compound C1 (1.0 g) and aqueous ammonia solution (density, 0.91 g/ml; 15 ml) were heated at 120° C. in a sealed tube for 10 hours. Volatile material was removed by evaporation and the residue azeotroped with toluene (2×20 ml). The residue was recrystallised from a mixture of methanol and ethyl acetate to give 2-methyl-1,5,7,8-tetrahydropyrano[4,3-b]-pyridin-4-one (B1) (0.70 g), as an off-white solid, m.p. >285° C.; NMR (d6 -DMSO): 2.2(s,3H), 2.45-2.6(m,2H), 3.8(t,2H), 4.3(t,2H), 5.8(s,1H) 11.1(br s, 1H).

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue azeotroped with toluene (2×20 ml)
  3. customThe residue was recrystallised from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-75dc97628b854dc9a838ab0faeb5121c
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

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