Ammonium formate → HCID 11630748, compound

HRID 2376276Notes

Reaction equation

HRID 2376276 reaction equation
C([NH:8][C:9]1[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]2[O:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:13]=2[C:26]=1[CH3:27])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[CH:23]([C:20]1[CH:21]=[CH:22][C:17]([CH:14]2[C:13]3[C:26]([CH3:27])=[C:9]([NH2:8])[C:10]([CH3:29])=[C:11]([CH3:28])[C:12]=3[O:16][CH2:15]2)=[CH:18][CH:19]=1)([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68711230HCID 68711230, compound

Product 1

HCID 11630748HCID 11630748, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 24 (900 mg, 2.33 mmol), 10%-palladium carbon (50% hydrous, 90 mg) and ammonium formate (294 mg, 4.66 mmol) in ethanol (10 mL) was heated under reflux for 2 hours. The solid material was removed and the filtrate was concentrated under reduced pressure. Water and ethyl acetate were added to the residue to separate the organic layer, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was crystallized from ethyl acetate-hexane to obtain 510 mg (yield 74%) of the title compound. Melting point: 171-173° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solid material was removed
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater and ethyl acetate were added to the residue
  6. customto separate the organic layer
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customto obtain a residue, which
  12. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a45087e956134846ab2a7ecfc2c7fb97
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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