Triethylamine → 2-[3-Methoxycarbonyl-5-(2-naphthoylamino)phenylamino]-3-nitropyridine

HRID 2086807Notes

Reaction equation

HRID 2086807 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.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[C:39](Cl)=[O:40].C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[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:3]=[C:2]([NH:1][C:39]([C:30]2[CH:31]=[CH:32][C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:29]=2)=[O:40])[CH:7]=1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium BicarbonateHCID 227240642-(3-Amino-5-methoxycarbonylphenylamino)-3-nitropyridine

Product 1

HCID 227243682-[3-Methoxycarbonyl-5-(2-naphthoylamino)phenylamino]-3-nitropyridineYield 86.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-(3-amino-5-methoxycarbonylphenylamino)-3-nitropyridine (550 mg) and triethylamine (0.3 ml) in 1,4-dioxane (10 ml) was added 2-naphthoyl chloride (0.40 g). The mixture was stirred at room temperature for 15 minutes, then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase containing orange solid was washed with water twice and the solid was collected to give 2-[3-methoxycarbonyl-5-(2-naphthoylamino)phenylamino]-3-nitropyridine (730 mg).

Workup

  1. additionThe organic phase containing orange solid
  2. washwas washed with water twice
  3. customthe solid was collected

Sources & evidence

ORD record
ord-03743c08b1af4b89abf8a99929f4781d
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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