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

HRID 1968459Notes

Reaction equation

HRID 1968459 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-one

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, the methanol was removed under reduced pressure. Water (2 L) was added to the residue. The precipitated solid was filtered and dried at 90° C. under reduced pressure to give the titled reference compound (44.02 g) as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-64dd99b6235b4f038286810c6263f767
Source dataset
uspto-grants-2013_04
Patent number
US08426406B2

Reaction notes

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