2-Naphthoyl chloride → Naphthalene-2-carboxamide

HRID 645943Notes

Reaction equation

HRID 645943 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].CO.[NH3:16]>>[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]([NH2:16])=[O:12]

Participants

3

Reactant 2

HCID 752462-Naphthoyl chlorideHCID 21705897Ammonia methanol

Product 1

HCID 75245Naphthalene-2-carboxamideYield 100%

Procedure

2-Naphthoyl chloride (2.21 g, 11.6 mmol) was dissolved in a MeOH/NH3 solution (2 M, 20 mL) and was allowed to stir overnight. Volatiles were removed and the resulting white solid was triturated with EtOAc. The solid was filtered and washed with cold EtOAc to yield a white solid which was used without further purification (1.98 g, 100% yield). m.p. 191-192° C. 1H NMR (CDCl3) δ 8.39 (s, 1H, ArH), 7.90 (4H, ArH), 7.57 (m, 2H, ArH). 13C NMR (CDCl3) δ 169.3, 135.0, 132.6, 130.5, 129.0, 128.6, 128.1, 127.9, 127.8, 126.9, 123.7. IR (nujol) vmax cm−1: 3400, 3210, 1650, 1628, 1512, 1510.

Workup

  1. customVolatiles were removed
  2. customthe resulting white solid was triturated with EtOAc
  3. filtrationThe solid was filtered
  4. washwashed with cold EtOAc
  5. customto yield a white solid which
  6. customwas used without further purification (1.98 g, 100% yield)

Sources & evidence

ORD record
ord-5d15b199a87d4b5aa5f66fb75f40be8d
Source dataset
uspto-grants-2010_04
Patent number
US07705022B2

Reaction notes

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