P-Anisidine → HCID 178487932, compound

HRID 876898Notes

Reaction equation

HRID 876898 reaction equation
[F:1][C:2]([F:9])([F:8])OCC([O-])=O.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1>>[CH3:10][O:11][C:12]1[CH:17]=[C:16]2[C:15](=[CH:14][CH:13]=1)[N:18]=[C:14]([C:2]([F:1])([F:8])[F:9])[CH:13]=[C:12]2[OH:11]

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 39872367HCID 39872367, compound

Product 1

HCID 178487932HCID 178487932, compoundYield 117.5%

Conditions

Temperature
150 °C

Procedure

A solution of trifluoro-3-oxa-butyrate (14.95 g, 81 mmol) and PPA (72 ml) was heated at 100° C. and then treated with p-anisidine (10 g, 81 mmol) portion wise. The reaction mixture was further heated to 150° C. and stirred for 2 h at 150° C. After cooling to RT, the reaction mixture was poured into a beaker containing ice water. After stirring for 20 min, the mixture was filtered, and the resulting solid was washed with water (˜3 L). The resulting pinkish-purple solid was dried under vacuum to provide 6-methoxy-2-(trifluoromethyl)quinolin -4-ol (11.58 g, 47.6 mmol, 58.6% yield), which was used without purification.

Workup

  1. temperatureAfter cooling to RT
  2. additionthe reaction mixture was poured into a beaker
  3. stirringAfter stirring for 20 min
  4. filtrationthe mixture was filtered
  5. washthe resulting solid was washed with water (˜3 L)
  6. customThe resulting pinkish-purple solid was dried under vacuum

Sources & evidence

ORD record
ord-dd92160ac76f4788a2162434c054664f
Source dataset
uspto-grants-2015_03
Patent number
US08987195B2

Reaction notes

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