Acetic Acid → HCID 59611569, compound

HRID 71913Notes

Reaction equation

HRID 71913 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 59611569HCID 59611569, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-485f66e30da4474a998a900222d6dad7
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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