Trifluoroacetic acid → HCID 22100449, compound

HRID 1457754Notes

Reaction equation

HRID 1457754 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH:10]1[CH:19](O)[C:18]2[C:13](=[CH:14][C:15]([CH3:21])=[CH:16][CH:17]=2)[O:12][CH2:11]1)=[O:8].C(OC(=O)C)(=O)C.FC(F)(F)C(O)=O>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([CH3:21])=[CH:16][CH:17]=2)[O:12][CH2:11]1)=[O:8]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 22100464HCID 22100464, compound

Product 1

HCID 22100449HCID 22100449, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

7.7 g (22 mmol) of 3-(5-chloro-2-methoxybenzamido)-7-methylchroman-4-ol were hydrogenated in a mixture of 80 ml of glacial acetic acid, 7.5 ml of acetic anhydride and 0.5 ml of trifluoroacetic acid with 0.5 g of Pd/C (10 %) at 25° C. under atmospheric pressure for about 3 hours. The catalyst was filtered off and the filtrate was concentrated to a small volume in vacuo. The residue was introduced into ice/water and the mixture was extracted several times with methylene chloride. The combined methylene chloride extracts were washed with sodium bicarbonate solution and water, dried and concentrated and the residue was recrystallized from diisopropyl ether. The 3-(5-chloro-2-methoxybenzamido)-7-methylchroman had a melting point of 97° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to a small volume in vacuo
  3. additionThe residue was introduced into ice/water
  4. extractionthe mixture was extracted several times with methylene chloride
  5. washThe combined methylene chloride extracts were washed with sodium bicarbonate solution and water
  6. customdried
  7. concentrationconcentrated
  8. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d4741df70aeb4b6d824ae59de532392a
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

Loading…