Ammonia → Naphthalene-2-carboxamide

HRID 1393339Notes

Reaction equation

HRID 1393339 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[NH3:14]>O1CCCC1>[C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:12])[NH2:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 752462-Naphthoyl chloride

Product 1

HCID 75245Naphthalene-2-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-naphthoyl chloride (5.70 g, 29.9 mmol) in tetrahydrofuran (60 ml) was added dropwise to a mixture of 28% aqueous ammonia (20 ml) and tetrahydrofuran (30 ml) with stirring under ice cooling, and the mixture was stirred at room temperature for 4 hrs. The solvent was distilled off under reduced pressure, and water was added to the residue. The precipitates were collected by filtration and dried to give 2-carbamoylnaphthalene (2.68 g, 52%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hrs
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-58366e10ef69463abb7f96ade83d3288
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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