HCID 86726460, compound → HCID 86726461, compound

HRID 1487633Notes

Reaction equation

HRID 1487633 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[N+:13]([O-])=O>CO.[Pd]>[NH2:13][C:4]1[CH:5]=[CH:6][C:7]([C:9]([NH:11][CH3:12])=[O:10])=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 86726460HCID 86726460, compound

Product 1

HCID 86726461HCID 86726461, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of 6-methoxy-N-methyl-5-nitropicolinamide (1 equiv) in MeOH (0.43 M) was stirred with palladium on carbon 10% w/w (10% by mass) under hydrogen (45 psi) for 1 h. The reaction mixture was filtered over Celite and concentrated. The crude product was purified by silica gel column chromatography (20-90% ethyl acetate (with 1% 1N ammonia in MeOH) in hexane). Concentration of the desired fractions under reduced pressure afforded the title compound (97%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.73 (d, J=4.69 Hz, 3H) 3.91 (s, 3H) 5.49 (br. s., 2H) 6.83 (d, J=7.81 Hz, 1H) 7.35 (d, J=7.81 Hz, 1H) 8.05 (q, J=4.82 Hz, 1H); MS (ESI) m/z 182.3 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel column chromatography (20-90% ethyl acetate (with 1% 1N ammonia in MeOH) in hexane)

Sources & evidence

ORD record
ord-fb8ab204a5a04251bbcdf7c7321f513e
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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