2-Bromo-4-chloro-6-methylbenzenamine → 7-Bromo-5-chloro-1H-indazole

HRID 855240노트

반응식

HRID 855240 반응식
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[N:11]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]2[C:3]=1[NH:4][N:11]=[CH:10]2

참가 물질

5

반응물 2

HCID 205437542-Bromo-4-chloro-6-methylbenzenamineHCID 23668193Sodium Nitrite

생성물 1

HCID 269676217-Bromo-5-chloro-1H-indazole수율 88.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

2.20 g (10 mmol) of 2-bromo-4-chloro-6-methyl aniline were dissolved in 125 ml acetic acid. 0.69 g (10 mmol) of sodium nitrite dissolved in 2 ml water were added dropwise. The reaction mixture was stirred at rt for 4 h. Acetic acid was evaporated and the residue dissolved in EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was several times evaporated with heptane to yield 2.04 g (88%) of 7-bromo-5-chloro-1H-indazol as a light brown solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.23 (s, 1H), 7.91 (s, 1H), 7.67 (s, 1H).

후처리

  1. additionwere added dropwise
  2. customAcetic acid was evaporated
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customevaporated with heptane

출처 및 근거

ORD 기록
ord-f841688c9249413cbd278adfafd336de
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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