p-Cyanobenzamide → HCID 73780984, compound

HRID 219899Notes

Reaction equation

HRID 219899 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5](F)[CH:4]=1.C(C1C=CC(C(N)=O)=CC=1)#[N:17]>>[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH2:17])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 76427p-CyanobenzamideHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 73780984HCID 73780984, compoundYield 94%

Procedure

The title compound was obtained following procedure described for Intermediate 1 step 2 but starting from 4-cyanobenzamide (396.1 mg, 2.71 mmol) (60° C. for 24 h). Solvents were removed under vacuum, solid residue was triturated in water, filtered and dried under vacuum to give the title compound as a white solid (460 mg, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 9.78 (bs, 1H), 7.98 (bs, 1H), 7.87-7.84 (m, 2H), 7.74-7.72 (m, 2H), 7.38 (bs, 1H), 5.88 (bs, 2H).

Workup

  1. customSolvents were removed under vacuum, solid residue
  2. customwas triturated in water
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-107701d0c40a40d5b54c1ad59efa29bc
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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