Acryloyl chloride → 6-Acryloylaminonaphthalene-2-carboxylic acid

HRID 2178187Notes

Reaction equation

HRID 2178187 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=2)[CH:3]=1.[C:15](Cl)(=[O:18])[CH:16]=[CH2:17]>CN(C=O)C.N1C=CC=CC=1.O>[C:15]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2)(=[O:18])[CH:16]=[CH2:17]

Participants

6

Reactant 2

HCID 13140Acryloyl chlorideHCID 27339546-Aminonaphthalene-2-carboxylic acid

Product 1

HCID 598604226-Acryloylaminonaphthalene-2-carboxylic acidYield 41.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-Amino-6-naphthoic acid (0.3 g, 1.6 mmol) in DMF (2 mL) and pyridine (0.3 mL) was added at 0° C., acryloyl chloride (0.15 g, 1.6 mmol). The resulting mixture was allowed to come to rt and stirred further for 2 h. After that it was poured in water (5 mL) and the solid separated was filtered and dried under reduced pressure to get the desired product (160 mg, 41.5%) as a pale brown solid. This solid was used in the next step without further purification.

Workup

  1. customto come to rt
  2. customthe solid separated
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-140a690b740c4dbda54287fedaa014ed
Source dataset
uspto-grants-2015_06
Patent number
US09067929B2

Reaction notes

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