Acetic Acid → HCID 59611569, 화합물

HRID 2039157노트

반응식

HRID 2039157 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 59611569HCID 59611569, 화합물수율 48.6%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 21974620tetrahydrofuran N,N-dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4ed89ff568b445568c32cf85bda2410b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575118B2

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