Phenyl phosphorodiamidate → 6-Methyl-5-phenylpyridin-2-amine

HRID 1995618Notes

Reaction equation

HRID 1995618 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(OP(N)([NH2:24])=O)C=CC=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([NH2:24])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 81954Phenyl phosphorodiamidateHCID 135028506-Methyl-5-phenylpyridin-2(1H)-one

Product 1

HCID 135028556-Methyl-5-phenylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 6-methyl-5-phenyl-2-pyridone (12.0 grams) and phenylphosphorodiamidate (14.4 grams) in 300 ml diphenyl ether was heated for 19-20 hours at approximately 220°-225° [250]° C. After cooling, the reaction mixture was chromatographed over silica gel with ethyl acetate. A total of 0.8 gram, of desired product was collected and recrystallized from dichloromethane/petroleum ether, m.p. 110°-113° C.

Workup

  1. temperaturewas heated for 19-20 hours at approximately 220°-225° [250]° C
  2. temperatureAfter cooling
  3. customthe reaction mixture was chromatographed over silica gel with ethyl acetate
  4. customA total of 0.8 gram, of desired product was collected
  5. customrecrystallized from dichloromethane/petroleum ether, m.p. 110°-113° C.

Sources & evidence

ORD record
ord-8748852fa503406d89d41ac41d6f08d2
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

Loading…