Dimethylformamide → Naphthalene-2-carboxamide

HRID 1444676Notes

Reaction equation

HRID 1444676 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]([OH:13])=O.C(Cl)(=O)C(Cl)=O.C[N:21](C=O)C>>[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]([NH2:21])=[O:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 71232-Naphthoic acidHCID 65578Oxalyl chloride

Product 1

HCID 75245Naphthalene-2-carboxamide

Procedure

To a solution of 2-naphthoic acid (25 g, 0.145 mol) in MC (200 ml), oxalyl chloride (38 ml, 0.4356 mol) and a catalytic amount of DMF were added and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was diluted with MC (200 ml), to which a solution of ammonium hydroxide in water (160 ml) was dropwise added at an ice bath temperature. After stirring for 1 hr, the precipitated product was collected by suction filtration, triturated in hexane and dried to obtain the title compound, which was used next step without further purification.

Workup

  1. customAfter the solvent was evaporated
  2. additionthe crude acyl chloride was diluted with MC (200 ml), to which a solution of ammonium hydroxide in water (160 ml)
  3. additionwas dropwise added at an ice bath temperature
  4. stirringAfter stirring for 1 hr
  5. filtrationthe precipitated product was collected by suction filtration
  6. customtriturated in hexane
  7. customdried

Sources & evidence

ORD record
ord-9c08dc1df57c420bb3347aaad14ccc0b
Source dataset
uspto-grants-2010_02
Patent number
US07662960B2

Reaction notes

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