N-Butyl propiolate → 5,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carboxylic acid, n-butyl ester

HRID 1112716

반응식

HRID 1112716 반응식
[N+:1](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])=[N-:2].[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])[C:14]#[CH:15]>C1(C)C(C)=CC=CC=1>[O:12]=[C:4]1[N:1]2[N:2]=[C:14]([C:13]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[CH:15]=[C:3]2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5]1

참가 물질

4

반응물 2

HCID 11366990N-Butyl propiolateHCID 136455454(3Z)-3-diazo-1H-indol-2-one

생성물 1

HCID 1363883965,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carboxylic acid, n-butyl ester

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

2.0 g (0.126 mole) of 3-diazo-oxindole is taken up in xylene (85 ml), treated with 1.2 equivalents of n-butyl propiolate (1.9 g) and refluxed under a stream of nitrogen for 17 hours in an oil bath. The light coral-colored precipitates that form are cooled and filtered off and washed with ether. Yield: 3.0 g, m.p. 190°-195°; 83.57% crude yield. The crude product is taken up in boiling absolute ethanol (250 ml), treated with activated carbon, filtered and concentrated down on a steam bath to a volume of ~75 ml. After cooling, tan-colored precipitates are filtered off and dried in a vacuum oven at room temperature for 4 hours. Yield: 2.2 g, m.p. 198°-200°.

후처리

  1. temperaturerefluxed under a stream of nitrogen for 17 hours in an oil bath
  2. customThe light coral-colored precipitates that form
  3. temperatureare cooled
  4. filtrationfiltered off
  5. washwashed with ether
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. concentrationconcentrated down on a steam bath to a volume of ~75 ml
  9. temperatureAfter cooling
  10. customtan-colored precipitates
  11. filtrationare filtered off
  12. customdried in a vacuum oven at room temperature for 4 hours

출처 및 근거

ORD 기록
ord-160d1fcd9e3142bf98d41123deef85aa
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04123532

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