Trifluoroacetic acid → 7-Methoxy-1,2,3,4-tetrahydroquinoline

HRID 2266645Notes

Reaction equation

HRID 2266645 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 59556816tert-Butyl 7-methoxy-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 162443887-Methoxy-1,2,3,4-tetrahydroquinolineYield 113.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methoxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (52 mg, 0.20 mmol) in dichloromethane (7 ml) at 0° C. was added dropwise trifluoroacetic acid (0.23 ml, 3.01 mmol) and the reaction mixture was then stirred at room temperature for 24 hours. The mixture was then made basic to pH 9 by dropwise addition of saturated aq. sodium carbonate solution. The mixture was extracted three times with a 1:1 mixture of ethyl acetate and tetrahydrofuran, the phases separated, and the organic phase dried over sodium sulphate and concentrated in vacuo to yield the title compound as a light brown oil (37 mg, 92%); MS (ISP): 164.4 ([M+H]+).

Workup

  1. extractionThe mixture was extracted three times
  2. additionwith a 1:1 mixture of ethyl acetate and tetrahydrofuran
  3. customthe phases separated
  4. dry with materialthe organic phase dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44708c30b19a4b92b0632658ea7a3036
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

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