Acetic Anhydride → 1-Methylethyl 5-(phenylmethoxy)-1H-indazole-3-carboxylate

HRID 1604630노트

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HRID 1604630 반응식
C([O-])(=O)C.[K+].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:8]=1[CH2:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23].C(OC(=O)C)(=O)C.C(O[N:41]=O)CC(C)C>C1C=CC=CC=1>[CH2:14]([O:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[NH:6][N:41]=[C:21]2[C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 21478799HCID 21478799, 화합물

생성물 1

HCID 196037391-Methylethyl 5-(phenylmethoxy)-1H-indazole-3-carboxylate수율 59.4%

시약·촉매·용매 1

HCID 241Benzene용매

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온도
80 °C

실험 절차

A mixture of potassium acetate (1.34 g), isopropyl 2-amino-5-benzyloxyphenylacetate (3.9 g) and acetic anhydride (4.0 g) in benzene (40 ml) was stirred at 80° C. After 30 minutes, isopentylnitrite (2.3 g) was added dropwise to the mixture over 15 minutes and then the mixture was stirred at same temperature for 4 hours. After cooling, insoluble mass was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol (30 ml) containing conc. sulphuric acid (0.5 ml) and the mixture was stirred at 80° C. for 3 hours. After cooling to room temperatures the resulting crystals were collected by filtration and washed with isopropyl ether to give isopropyl 5-benzyloxy-1H-indazole-3-carboxylate (2.4 g).

후처리

  1. stirringthe mixture was stirred at same temperature for 4 hours
  2. temperatureAfter cooling
  3. filtrationinsoluble mass was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in isopropyl alcohol (30 ml)
  6. additioncontaining conc. sulphuric acid (0.5 ml)
  7. stirringthe mixture was stirred at 80° C. for 3 hours
  8. temperatureAfter cooling to room temperatures the resulting crystals
  9. filtrationwere collected by filtration
  10. washwashed with isopropyl ether

출처 및 근거

ORD 기록
ord-b5aca1c87310416d8e84518bd59f8223
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994378

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