Acetic Acid → HCID 178524398, compound

HRID 2073700Notes

Reaction equation

HRID 2073700 reaction equation
[C:1]1([C:20]([OH:22])=[O:21])[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]=2[C:4]([C:17](O)=[O:18])=[CH:3][CH:2]=1.C(N(CC)CC)C.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)(=O)C>O>[C:31]1([N:30]=[C:17]([C:4]2[C:5]3[C:6]([C:14]([OH:16])=[O:15])=[CH:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[C:10]=3[C:1]([C:20]([OH:22])=[O:21])=[CH:2][CH:3]=2)[OH:18])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 6115AnilineHCID 8471TriethylamineHCID 314221,4,5,8-Naphthalenetetracarboxylic acid

Product 1

HCID 178524398HCID 178524398, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

53.6 g of naphthalene-1,4,5,8-tetracarboxylic acid dianhydride (0.2 mol) or 60.8 g of naphthalene-1,4,5,8-tetracarboxylic acid (0.2 mol) are dissolved in 1 l of water at 90° C. with addition of 84 g of triethylamine (0.9 mol), treated with 18.6 g of aniline (0.2 mol) with stirring and adjusted to pH 6 by dropwise addition of about 20 ml of glacial acetic acid at 90° C. The mixture is stirred for about 8 hours at 90° C., the pH value being maintained between 7 and 6 by further dropwise addition of glacial acetic acid (6 ml in total). The mixture is cooled to room temperature, a few undissolved components are filtered off, and the filtrate is adjusted to pH 1 by dropwise addition of about 160 ml of concentrated hydrochloric acid. The crystalline precipitate is filtered off by suction, washed with water until the washings have pH 5, and dried at 70° C. in vacuo. 63 g (87% of theory) of naphthalene-1,4,5,8-tetracarboxylic acid monophenylimide are obtained as an almost colourless crystalline powder of melting point >300° C.

Workup

  1. stirringThe mixture is stirred for about 8 hours at 90° C.
  2. filtrationa few undissolved components are filtered off
  3. additionthe filtrate is adjusted to pH 1 by dropwise addition of about 160 ml of concentrated hydrochloric acid
  4. filtrationThe crystalline precipitate is filtered off by suction
  5. washwashed with water until the washings
  6. customdried at 70° C. in vacuo

Sources & evidence

ORD record
ord-fbd8d7e713dd4e8b821a19ae6f543862
Source dataset
uspto-grants-1990_04
Patent number
US04919848

Reaction notes

Loading…