Methyl 2-(2-benzyloxyphenyl)-5-nitrobenzoate → 8-Aminobenzo[c]chromen-6-one

HRID 909286Notes

Reaction equation

HRID 909286 reaction equation
C(O[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][C:16]=1[C:17]([O:19]C)=[O:18])C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[NH2:25][C:22]1[CH:23]=[CH:24][C:15]2[C:10]3[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:19][C:17](=[O:18])[C:16]=2[CH:21]=1

Participants

5

Reactant 1

HCID 58026868Methyl 2-(2-benzyloxyphenyl)-5-nitrobenzoate

Product 1

HCID 233789368-Aminobenzo[c]chromen-6-oneYield 73%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-benzyloxyphenyl)-5-nitrobenzoate (Reference Compound No. 1-1-(1), 21.0 g, 57.8 mmol) was dissolved in a mixture of methanol (135 mL) and tetrahydrofuran (90 mL), then 5% palladium on charcoal (2.19 g) was added thereto, and then the reaction mixture was stirred under hydrogen atmosphere at room temperature overnight. After the unsoluble materials were filtered, the filtrate was removed under reduced pressure. A mixture of ethyl acetate and hexane was added to the obtained residue, and then the mixture was filtered to give the titled reference compound (8.92 g) as a pale yellow solid. (Yield 73%)

Workup

  1. filtrationAfter the unsoluble materials were filtered
  2. customthe filtrate was removed under reduced pressure
  3. additionA mixture of ethyl acetate and hexane
  4. additionwas added to the obtained residue
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-abceab85593e42bc949466890ab36a64
Source dataset
uspto-grants-2011_09
Patent number
US08017775B2

Reaction notes

Loading…