Acetic Acid → HCID 59611569、化合物

HRID 71913ノート

反応式

HRID 71913 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=3)[O:11][CH2:10][C:9]=2[CH:21]=1)=[O:4].C(O)(=O)C>C1COCC1.CN(C=O)C.[Zn]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=3)[O:11][CH2:10][C:9]=2[CH:21]=1)=[O:4]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 596110693-Nitro-6H-benzo[c]chromene-8-carboxylic acid methyl ester

生成物 1

HCID 59611569HCID 59611569、化合物収率 48.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

To the solution of 3-Nitro-6H-benzo[c]chromene-8-carboxylic acid methyl ester (690 mg) in THF/DMF (5 ml/5 ml) was added acetic acid (10 ml), followed by slow addition of Zinc (800 mg). The mixture was stirred for 12 hours and solvents were removed under reduced pressure. The mixture was diluted with EtOAc, and 0.2 N sodium hydroxide solution was added until pH=10. The organic layer was separated and was washed with water and brine and dried with Na2SO4. Concentration and purification by flash column chromatography (DCM/EtOAc) gave 3-Amino-6H-benzo[c]chromene-8-carboxylic acid methyl ester (300 mg).

後処理

  1. customsolvents were removed under reduced pressure
  2. additionThe mixture was diluted with EtOAc, and 0.2 N sodium hydroxide solution
  3. additionwas added until pH=10
  4. customThe organic layer was separated
  5. washwas washed with water and brine
  6. dry with materialdried with Na2SO4
  7. concentrationConcentration and purification by flash column chromatography (DCM/EtOAc)

出典と根拠

ORDレコード
ord-485f66e30da4474a998a900222d6dad7
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

反応ノート

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