Trifluoroacetic acid → HCID 19610515, compound

HRID 977028Notes

Reaction equation

HRID 977028 reaction equation
[CH3:1][N:2](C(OC(C)(C)C)=O)[NH:3][C:4]([C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>ClCCl.C1(OC)C=CC=CC=1>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH3:1][NH:2][NH:3][C:4]([C:6]1[CH:17]=[CH:16][C:9]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70055592HCID 70055592, compound

Product 1

HCID 19610515HCID 19610515, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a stirred suspension of the product of step (a) (2.9 g) in a mixture of dichloromethane (20 ml) and anisole (2 ml) at 0°-5° C. was added trifluoroacetic acid (27 ml). The resultant solution was stirred at low temperature for 20 minutes and then at ambient temperature for 2.5 hours. The reaction mixture was evaporated and the residue was triturated with dry ether. The solid was collected and washed with ether to give methyl 4-(3-methylcarbazoyl)phenoxyacetate trifluoroacetate salt (2.9 g), as a white solid; m.p. 121°-123° C.; NMR Spectrum (DMSO-d6) 2.80 (3H, s), 3.70 (3H, s), 4.93 (2H, s), 7.10 (2H, d), 7.85 (2H, d), 10.80-11.70 (1H, br s); Mass Spectrum m/Z 239 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated with dry ether
  3. customThe solid was collected
  4. washwashed with ether

Sources & evidence

ORD record
ord-1b45186288f04193a5fa35c78d5e8d3a
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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