Ammonia methanol → HCID 66799693, compound

HRID 2172726Notes

Reaction equation

HRID 2172726 reaction equation
[NH3:1].CO.C([O:6][C:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:17]=2)[N:10]=1)=O)C>CO>[Cl:15][C:13]1[CH:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:17]=2)[N:10]=[C:9]([C:7]([NH2:1])=[O:6])[CH:14]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 66799594HCID 66799594, compound

Product 1

HCID 66799693HCID 66799693, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50-ml vial with a screw-top septum, 4-chloro-6-[3-(4-fluoro-phenoxy)-phenyl]-pyridine-2-carboxylic acid ethyl ester (0.445 g) was dissolved in 3 ml methanol. 7N NH3/MeOH (6 ml) was added to the solution and stirred for 3 hours, at which time the reaction was complete. The reaction mixture was concentrated under reduced pressure and the residue was suspended in about 3 ml methanol. The suspension was collected by vacuum filtration and washed with cold methanol to provide 0.267 g of 4-chloro-6-[3-(4-fluoro-phenoxy)-phenyl]-pyridine-2-carboxylic acid amide as a very pure yellow solid (65% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe suspension was collected by vacuum filtration
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-d61ab35dade74d17a77f5b6b85ee173c
Source dataset
uspto-grants-2015_06
Patent number
US09056832B2

Reaction notes

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