Sodium Hydroxide → 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

HRID 85411ノート

反応式

HRID 85411 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67468514Methyl 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylate

生成物 1

HCID 674688776-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylate (0.22 g, 0.871 mmol) was dissolved in methanol (6 mL) and THF (1 mL), followed by addition of NaOH (1.451 mL, 4.35 mmol) via syringe. The contents were stirred at RT for 3 h. The volatiles were removed in vacuo, the contents diluted with water, and then slowly acidifed to pH 4-5 by addition of 1M HCl (solid precipitation occurred). The contents were then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The collected solid was dried under hi-vac for 2 h, and collected as 0.19 g (90%). 1H NMR (400 MHz, DMSO-d6) ppm 1.47 (d, J=6.57 Hz, 6H) 5.09 (quin, J=6.57 Hz, 1H) 7.70 (d, J=1.52 Hz, 1H) 8.25 (s, 1H) 8.40 (s, 1H), 13.54 (br. s., 1H).

後処理

  1. customThe volatiles were removed in vacuo
  2. additionthe contents diluted with water
  3. additionslowly acidifed to pH 4-5 by addition of 1M HCl (solid precipitation occurred)
  4. extractionThe contents were then extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe collected solid was dried under hi-vac for 2 h
  10. customcollected as 0.19 g (90%)

出典と根拠

ORDレコード
ord-5e44074d612d4126b83dd0971dc2bd6c
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

反応ノート

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