Ammonium Hydroxide → HCID 66913663, compound

HRID 2104591Notes

Reaction equation

HRID 2104591 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:29])([F:28])[F:27])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:31]>O>[NH2:31][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[C:26]([F:27])([F:28])[F:29])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66914289HCID 66914289, compound

Product 1

HCID 66913663HCID 66913663, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

(4-Fluorophenyl)[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (0.631 g, 1.60 mmol) and ammonium hydroxide (9 mL) are heated in a steel pressure vessel at 150° C. overnight. The cooled reaction is poured into water, extracted with methylene chloride, and concentrated in vacuo. The resulting solid into DMSO (2 mL) and ammonium hydroxide (8 mL) is heated in the steel bomb at 150° C. overnight and worked up as above. The product is purified by chromatography eluting with 30:70 ethyl acetate:hexane to yield the title compound as a solid (0.344 g). MS (ESI) m/z 393; HRMS: calcd for C23H15F3N2O—H, 391.10582; found (ESI, [M−H]−), 391.1054.

Workup

  1. customThe cooled reaction
  2. extractionextracted with methylene chloride
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by chromatography
  5. washeluting with 30:70 ethyl acetate

Sources & evidence

ORD record
ord-38c815c79789428088aad974155a2706
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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