1,2-Dichlorobenzene → HCID 141613330, compound

HRID 576449Notes

Reaction equation

HRID 576449 reaction equation
[OH:1][C:2]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]2[C:3]=1[C:4](=O)[C:5]1[CH:6]=[C:7]([C:25]([OH:27])=[O:26])[C:8]([C:22]([OH:24])=[O:23])=[CH:9][C:10]=1[C:11]2=[O:21].[CH:29]([C:32]1[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]([CH3:41])[CH3:40])[C:33]=1[NH2:34])([CH3:31])[CH3:30].ClC1C=CC=CC=1Cl>O>[CH:39]([C:35]1[CH:36]=[CH:37][CH:38]=[C:32]([CH:29]([CH3:31])[CH3:30])[C:33]=1[N:34]=[C:4]1[C:3]2[C:12](=[C:13]([OH:20])[C:14]3[C:19]([C:2]=2[OH:1])=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[O:21])[C:10]2[CH:9]=[C:8]([C:22]([OH:24])=[O:23])[C:7]([C:25]([OH:27])=[O:26])=[CH:6][C:5]1=2)([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 32484DiisopropylanilineHCID 140543976HCID 140543976, compound2×

Product 1

HCID 141613330HCID 141613330, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g (1.32 mmoles) of 6,11-Dihydroxy-naphthacene-5,12-dione-2,3-dicarboxylic acid (product of Example 8), 0.28 g (1.58 mmoles) of 2,6-diisopropylaniline, and 25 ml of o-dichlorobenzene are refluxed for 4 h with azeotropic removal of the reaction water. The mixture is filtered while hot, and the filtrate is kept at 25° for 18 h. The precipitate is washed with hot hexane and dried to give 0.35 g (51%) of red crystals, m.p. 328-330°.

Workup

  1. filtrationThe mixture is filtered while hot, and the filtrate
  2. washThe precipitate is washed with hot hexane
  3. customdried

Sources & evidence

ORD record
ord-f6fc036f7d06414690eeb575fd648cb5
Source dataset
uspto-grants-2015_05
Patent number
US09039946B2

Reaction notes

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