Acetic Acid → HCID 59611569, 화합물

HRID 79859노트

반응식

HRID 79859 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-3e98992a74e94ac3a7e8ba9f33cb9849
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841278B2

반응 노트

불러오는 중…