Ethanamine, 2,2,2-trifluoro- → Methyl 2-((2,2,2-trifluoroethyl)amino)quinoline-7-carboxylate

HRID 881003Notes

Reaction equation

HRID 881003 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N+:12]2[O-])=[CH:7][CH:6]=1)=[O:4].[F:16][C:17]([F:21])([F:20])[CH2:18][NH2:19].CC1C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>ClCCl>[F:16][C:17]([F:21])([F:20])[CH2:18][NH:19][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[N:12]=1

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 77773Toluene-p-sulphonic anhydrideHCID 674916957-(Methoxycarbonyl)quinoline 1-oxide

Product 1

HCID 67491717Methyl 2-((2,2,2-trifluoroethyl)amino)quinoline-7-carboxylateYield 205.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(methoxycarbonyl)quinoline 1-oxide (200 mg, 0.984 mmol) and 2,2,2-trifluoroethylamine (292 mg, 0.295 mmol) at 0° C. was added 4-methylbenzenesulphonic anhydride (964 mg, 2.95 mmol) portionwise over a period of 45 minutes. The reaction was allowed to warm up to room temperature and stirred overnight. The reaction was diluted with dichloromethane and washed with a saturated solution of ammonium chloride. The aqueous layer was extracted into dichloromethane (1×). The organics were combined and washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography gave the title compound (172 mg, 62%). +ESI (M+H) 285.1

Workup

  1. washwashed with a saturated solution of ammonium chloride
  2. extractionThe aqueous layer was extracted into dichloromethane (1×)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2f293e6917f94ed88f0b3cde54a540e0
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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