HCID 22057952, compound → N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide

HRID 1357701Notes

Reaction equation

HRID 1357701 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=2)=[O:10])=[CH:4][C:3]=1[N+:23]([O-])=O.[H][H]>[Pd].CO>[NH2:23][C:3]1[CH:4]=[C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:12]=2)=[O:10])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 22057952HCID 22057952, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17904941N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamideYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Under argon, 5% palladium on carbon (850 mg) was added to N-(4-methyl-3-nitrophenyl)-2-morpholinopyridine-4-carboxamide (8.5 g) in methanol (300 ml). Hydrogen gas was introduced to the reaction via a balloon and stirred at ambient temperature for 18 hours. Methanol (200 ml) was added and the reaction mixture was filtered through celite. The filtrate was evaporated, then stirred in ethyl acetate, filtered again and washed with a small amount of methanol to yield N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide (5.12 g); NMR: 2.01 (s, 3H), 3.52 (m, 4H), 3.73 (m, 4H), 4.83 (s, 2H), 6.78 (d, 1H), 6.84 (d, 1H) 7.04-7.08 (m, 2H), 7.20 (s, 1H), 8.24 (d, 1H), 9.95 (s, 1H); m/s: M+H+ 313.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. customThe filtrate was evaporated
  3. stirringstirred in ethyl acetate
  4. filtrationfiltered again
  5. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-540345902e5f4d38bee81c5b7c65921f
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

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