Trifluoroacetic acid → HCID 68829781, compound

HRID 1986444Notes

Reaction equation

HRID 1986444 reaction equation
C([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:10]([C:20]#[N:21])=[C:9]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])(C)(C)C.FC(F)(F)C(O)=O>O1CCCC1>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([OH:5])[CH:7]=2)[N:12]=[C:11]([CH2:16][CH:17]([CH3:18])[CH3:19])[C:10]=1[C:20]#[N:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68831716HCID 68831716, compound

Product 1

HCID 68829781HCID 68829781, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-tert-butoxy-4-(2-fluorophenyl)-2-isobutylquinoline-3-carbonitrile (0.22 g, 0.58 mmol) in tetrahydrofuran (1 ml) was added trifluoroacetic acid (5 ml), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated and the obtained crude crystals were recrystallized from n-hexane-ethyl acetate to give 4(2-fluorophenyl)-6-hydroxy-2-isobutylquinoline-3-carbonitrile (0.17 g, yield 92%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained crude crystals
  3. customwere recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-2a5fb87cd9414f6aa53e1afa43d66ea3
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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