Ammonia → HCID 59403018, compound

HRID 538527Notes

Reaction equation

HRID 538527 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)[CH:5]=1.[NH3:18]>O>[N:12]1([CH2:11][O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([NH2:18])=[O:2])[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59402928Methyl 3-(1H-pyrazol-1-ylmethoxy)benzoate

Product 1

HCID 59403018HCID 59403018, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

3-(Pyrazol-1-ylmethoxy)-benzoic acid methyl ester (250 mg, 1.1 eq.) was taken in a pressure vessel along with 5 ml of aq. ammonia, heated at 110° C. for 12 hr. reaction mass was then poured in water (25 ml), extracted with dichloromethane (25 ml×4). Organic layer was dried over sodium sulphate and concentrated to obtain crude solid. Product was purified by column chromatography using 80% EtOAc-DCM as an eluent over 230-400 mesh silica gel. Pure product was obtained as solid powder (50 mg, 19%). 1H NMR (DMSO-d6, 400 MHz with D2O): δ 6.12 (s, 2H), 6.33 (m, 1H), 7.25 (m, 1H), 7.37 (m, 1H), 7.41 (m, 1H), 7.51 (m, 1H), 7.56 (m, 2H), 7.95 (br s, 1H), 7.99 (m, 1H). MS ES+ (218.0, 235.0—Ammonium adduct), HPLC (method 7) Rt=9.08 min.

Workup

  1. customreaction mass
  2. extractionextracted with dichloromethane (25 ml×4)
  3. dry with materialOrganic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customto obtain crude solid
  6. customProduct was purified by column chromatography

Sources & evidence

ORD record
ord-d1a35428b201424ba943d8e00b1e88d4
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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