3-Hydroxy-8-nitrobenzo[c]chromen-6-one → 8-Amino-3-hydroxybenzo[c]chromen-6-one

HRID 2091539Notes

Reaction equation

HRID 2091539 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:7]=3[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1>CO.CN(C)C=O.[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:6]2[C:5]3[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=3)[O:9][C:8](=[O:12])[C:7]=2[CH:13]=1

Participants

5

Reactant 1

HCID 579905963-Hydroxy-8-nitrobenzo[c]chromen-6-one

Product 1

HCID 579905888-Amino-3-hydroxybenzo[c]chromen-6-oneYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-8-nitrobenzo[c]chromen-6-one (Reference Compound No. 1-1-(2), 52.01 g, 202 mmol) was dissolved in methanol (150 mL)-N,N-dimethylformamide (600 mL), 10% palladium on charcoal (5.00 g) was added thereto, and then the reaction mixture was stirred under hydrogen atmosphere (3 kgf/cm2) at room temperature overnight. After the unsoluble materials were filtered out, the methanol was removed under reduced pressure. Water (2 L) was added to the residue. The precipitated solid was filtered off and dried at 90° C. under reduced pressure to give the titled reference compound (44.02 g) as a pale yellow solid. (Yield 96%)

Workup

  1. additionwas added
  2. filtrationAfter the unsoluble materials were filtered out
  3. customthe methanol was removed under reduced pressure
  4. additionWater (2 L) was added to the residue
  5. filtrationThe precipitated solid was filtered off
  6. customdried at 90° C. under reduced pressure

Sources & evidence

ORD record
ord-a7aca1cc4e924a4b9280f876555ead02
Source dataset
uspto-grants-2013_05
Patent number
US08440660B2

Reaction notes

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