Methyl 3-amino-4-methylbenzoate → methyl 1H-indazole-6-carboxylate

HRID 508200

反応式

HRID 508200 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[N:13]([O-])=O.[Na+]>CC(O)=O.O>[NH:1]1[C:2]2[C:11](=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[CH:12]=[N:13]1

参加物

5

反応物 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23668193Sodium Nitrite

生成物 1

HCID 286535methyl 1H-indazole-6-carboxylate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a solution of methyl 3-amino-4-methylbenzoate D-1 (5.0 g, 30 mmol) in AcOH (140 mL) at 0° C. was added a solution of sodium nitrite (2.1 g, 30 mmol) in H2O (3.5 mL). After addition, the mixture was stirred at rt for 24 h. Then half of the solvent was removed under reduced pressure and the resulting mixture was diluted with H2O, and extracted with EtOAc. The combined organics were washed H2O and brine, and concentrated to give the title compound. LCMS (ESI) calc'd for C9H9N2O2 [M+H]+: 177. found 177.

後処理

  1. additionAfter addition
  2. customThen half of the solvent was removed under reduced pressure
  3. additionthe resulting mixture was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed H2O and brine
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5b4f708b0c6244d7a112f0e8c44dfad3
出典データセット
uspto-grants-2015_08
特許番号
US09095583B2

関連ノート

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