Dimethylformamide → 3-Cyano-1-naphthoyl chloride

HRID 749435Notes

Reaction equation

HRID 749435 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=O)[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].C(Cl)(=O)C([Cl:19])=O.CN(C=O)C>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([Cl:19])=[O:15])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 111715903-cyanonaphthalene-1-carboxylic Acid

Product 1

HCID 226366863-Cyano-1-naphthoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyano-1-naphthoic acid (see Bioorg. Med. Chem. Lett. 2001, 2769; 1.1 g, 5.6 mmol) was slurried in CH2Cl2 (10 mL) and then oxalyl chloride was added with stirring. A drop of DMF was added and the mixture stirred at room temperature overnight under nitrogen. The solvent was removed by evaporation and there was obtained 1.2 g (100%) of 3-cyano-1-naphthoyl chloride as a pale yellow solid. 1H NMR (300 MHz, CDCl3): 7.7-7.8 (m, 1H), 7.8-7.9 (m, 1H), 8.0-8.1 (m, 1H), 8.5 (s, 1H), 8.7 (s, 1H), 8.8 (d, 1H).

Workup

  1. stirringthe mixture stirred at room temperature overnight under nitrogen
  2. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-88498fb6aa8249e595eabcc7a038119a
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

Loading…