3-Nitroaniline → N-(3-nitrophenyl)-2-naphthalenecarboxamide

HRID 2231001Notes

Reaction equation

HRID 2231001 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28](Cl)=[O:29].C(=O)(O)[O-].[Na+]>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:28]([C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)=[O:29])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 7780003N-(3-nitrophenyl)-2-naphthalenecarboxamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3-nitroaniline (2.07 g) and triethylamine (2.3 ml) in 1,4-dioxane (40 ml) was added 2-naphthoyl chloride (3.00 g) and the mixture was stirred at room temperature for 30 minutes. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate three times. The combined organic phase was 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 N-(3-nitrophenyl)-2-naphthalenecarboxamide (3.02 g).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phase was washed 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-4fad885830bd408fa46cd4ddfc86347d
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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