Trifluoroacetic acid → 2-[N-(2-Benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylic Acid

HRID 355804Notes

Reaction equation

HRID 355804 reaction equation
[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:10]=1[CH2:11][CH2:12][N:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:18][N:17]=1)[CH2:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:10]=1[CH2:11][CH2:12][N:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][N:17]=1)[CH2:14][CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22675480tert-Butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylate

Product 1

HCID 226755432-[N-(2-Benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylic AcidYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylate (800 mg) and trifluoroacetic acid (20 ml) in dichloromethane (20 ml) was heated at reflux for 30 minutes. The solvent was evaporated and the residue crystallised from a mixture of dichloromethane and diethyl ether (1:2) to give the title compound (600 mg) mpt 214° C. (decomp).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was evaporated
  3. customthe residue crystallised from a mixture of dichloromethane and diethyl ether (1:2)

Sources & evidence

ORD record
ord-6f26939c49d241df8ec19af555b2ac81
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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