2,6-Naphthalenedicarboxylic acid → HCID 19603324, compound

HRID 1604531Notes

Reaction equation

HRID 1604531 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14]([OH:16])=O.Cl.CN.O[N:21]1[C:25]2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH3:25][NH:21][C:14]([C:2]1[CH:1]=[C:10]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[C:7]([C:11]([OH:13])=[O:12])[CH:8]=[CH:9]2)=[O:16]

Participants

7

Reactant 4

HCID 143572,6-Naphthalenedicarboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochloride

Product 1

HCID 19603324HCID 19603324, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of naphthalene-2,6-dicarboxylic acid (5 g), methylamine hydrochloride (1.64 g) and 1-hydroxybenzotriazole (3.75 g) in dimethylformamide (50 ml) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (3.79 g) under ice-cooling. The mixture was stirred for 1 hour at the same temperature and then at ambient temperature overnight. The mixture was diluted with water, and the precipitates were collected by filtration to give 6-(methylcarbamoyl)naphthalene-2-carboxylic acid (4.07 g).

Workup

  1. temperaturecooling
  2. customat ambient temperature
  3. customovernight
  4. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-5036c5216f8e4b7c986b7266392cee88
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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