Formamidine acetate → 5-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile

HRID 462710노트

반응식

HRID 462710 반응식
[C:1]([C:4]1[CH:5]=[C:6]([C:16]#[N:17])[C:7](=[O:15])[NH:8][C:9]=1[CH:10]=[CH:11][N:12](C)C)(=O)[CH3:2].C(O)(=O)C.C(N)=N>CN(C)C=O>[CH3:2][C:1]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:16]#[N:17])[C:7](=[O:15])[NH:8]2

참가 물질

4

반응물 2

HCID 160693Formamidine acetateHCID 53841137HCID 53841137, 화합물

생성물 1

HCID 57130685-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile수율 103.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

E-1. 1,2-Dihydro-5-methvl-2-oxo-1,6-naphthyridine-3-carbonitrile--A mixture containing 33.2 g of 5-acetyl-1,2-dihydro-6-(2-dimethylaminoethenyl)-2-oxo-3-pyridincarbonitrile, 32.1 g of formamidine acetate and 300 ml of dimethylformamide was heated in a oil bath at 120°-130° C. for 3 hours, the original yellow solid dissolving and dark solution resulting. The reaction mixture was evaporated to dryness and then treated with 400 ml of water followed by 30 ml of acetic acid. The resulting insoluble solid was collected, washed with water, air-dried, recrystallized from dimethylformamide and dried at 90° C. to yield 27.4 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile as a compound containing 1/2 mole of dimethylformamide, m.p. 278°-280° C. with decomposition.

후처리

  1. temperaturewas heated in a oil bath at 120°-130° C. for 3 hours
  2. dissolutionthe original yellow solid dissolving
  3. customdark solution resulting
  4. customThe reaction mixture was evaporated to dryness
  5. additiontreated with 400 ml of water
  6. customThe resulting insoluble solid was collected
  7. washwashed with water
  8. customair-dried
  9. customrecrystallized from dimethylformamide
  10. customdried at 90° C.

출처 및 근거

ORD 기록
ord-1a1c203ab9f4465a9e7a734f7bd59abf
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04517190

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