Acetic Anhydride → 2-(3-Acetylamino-5-methoxycarbonylphenylamino)-3-nitropyridine

HRID 2230984Notes

Reaction equation

HRID 2230984 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30].C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.O1CCOCC1.C(OCC)(=O)C>[C:29]([NH:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1)(=[O:31])[CH3:30]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 227240642-(3-Amino-5-methoxycarbonylphenylamino)-3-nitropyridine

Product 1

HCID 227241872-(3-Acetylamino-5-methoxycarbonylphenylamino)-3-nitropyridine

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-[3-amino-5-methoxycarbonylphenylamino]-3-nitropyridine (1.10 g), triethylamine (0.6 ml) and 4-dimethylaminopyridine (14 mg) in 1,4-dioxane (15 ml) was added acetic anhydride (0.40 ml). The mixture was stirred at room temperature for 20 hours, then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-(3-acetylamino-5-methoxycarbonylphenylamino)-3-nitropyridine (1.21 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-1079ab6e7f0142018e98ba50425085ae
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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