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

HRID 2039519Notes

Reaction equation

HRID 2039519 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.[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

4

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 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Hydroxy-8-nitrobenzo[c]chromen-6-one (Reference Compound No. 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. filtrationAfter the unsoluble materials were filtered out
  2. customthe methanol was removed under reduced pressure
  3. additionWater (2 L) was added to the residue
  4. filtrationThe precipitated solid was filtered off
  5. customdried at 90° C. under reduced pressure

Sources & evidence

ORD record
ord-1d01799530ad4af28ffd5c9fa50a7ea8
Source dataset
uspto-grants-2013_11
Patent number
US08580784B2

Reaction notes

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