Oxalyl chloride → HCID 13351908, compound

HRID 1924431Notes

Reaction equation

HRID 1924431 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]C=1C(O)=O>C(Cl)Cl>[CH3:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 6087221-Methoxy-2-naphthoic acid

Product 1

HCID 13351908HCID 13351908, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (118 μL, 1.35 mmol) was added dropwise to a partial solution of 1-methoxy-2-naphthoic acid (3-A) (210 mg, 1.04 mmol) in methylene chloride (2.0 mL). The mixture bubbled for several min and then cleared. After stirring for 3 h at room temperature, the mixture was evaporated in vacuo to give 1-methoxy-2-naphthoyl chloride (3-B). Methylene chloride (5.0 mL) was added followed by methylamine hydrochloride (330 mg, 5.05 mmol) and N,N-diisopropylethylamine (441 μL, 2.53 mmol) and the resulting mixture stirred at room temperature 18 h. Methylene chloride was added and the mixture washed with water, 1N HCl, 10% NaHCO3, brine, dried (MgSO4) and concentrated in vacuo to provide 1-methoxy-N-methyl-2-naphthamide (3-C).

Workup

  1. customThe mixture bubbled for several min
  2. customthe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-cfc4a0d1115241a682a2c424ade03b4c
Source dataset
uspto-grants-2012_05
Patent number
US08178546B2

Reaction notes

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