Tetrahydrofuran → HCID 68962942, compound

HRID 2191779Notes

Reaction equation

HRID 2191779 reaction equation
O1CCCC1.[F:6][C:7]1[CH:36]=[CH:35][C:10]([NH:11][C:12]2[CH:24]=[C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N+:32]([O-])=O)[CH:22]=[CH:21][C:13]=2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][CH:8]=1>[C].[Pd].C(OCC)(=O)C>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:23]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:36][CH:35]=2)[CH:24]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68962723HCID 68962723, compound

Product 1

HCID 68962942HCID 68962942, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of tetrahydrofuran 10 mL and ethyl acetate 5.0 mL of tert-butyl 2-(4-fluoroanilino)-4-(2-nitroanilino)benzoate 0.35 g was added 10% palladium-carbon 74 mg, it was stirred under hydrogen atmosphere at room temperature for 4 hours and 30 minutes, and subsequently it was stirred at 34° C. for 4 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and the solvent was removed under reduced pressure. Hexane was added to the obtained residue, and solid matter was filtrated to give tert-butyl 4-((2-aminophenyl)amino)-2-(4-fluoroanilino)benzoate 0.15 g of a white solid.

Workup

  1. stirringsubsequently it was stirred at 34° C. for 4 hours
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationinsoluble matter was filtrated
  4. customthe solvent was removed under reduced pressure
  5. additionHexane was added to the obtained residue, and solid matter
  6. filtrationwas filtrated

Sources & evidence

ORD record
ord-106b551b522f4f4c94a4818c7627ea3a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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