Acryloyl chloride → 6-Acryloylaminonaphthalene-2-carboxylic acid

HRID 885647Notes

Reaction equation

HRID 885647 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-9c171b1b661144da938923f1dddca3ad
Source dataset
uspto-grants-2012_08
Patent number
US08242271B2

Reaction notes

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