Chlorosuccinimide → HCID 13375410, compound

HRID 1381796Notes

Reaction equation

HRID 1381796 reaction equation
[C:1]1([C:15]([OH:17])=[O:16])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[Cl:18]N1C(=O)CCC1=O>CN1CCCC1=O.O>[Cl:18][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:14]2[C:5]=1[CH:4]=[CH:3][CH:2]=[C:1]2[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 1507891-Anthracenecarboxylic Acid

Product 1

HCID 13375410HCID 13375410, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Anthracene-1-carboxylic acid (15B, 24g, 0.108 mol) was treated with N-chlorosuccinimide (Aldrich, 24 g, 0.18 mol) in N-methylpyrrolidinone (Eastman, 600 mL) and heated under N2 at 90° for 1.5 h. The reaction mixture was diluted with H2O (3.5 L), filtered, dried, and the precipitate recrystallized from EtOAc to afford 16.41 g (59%) of 10-chloroanthracene-1-carboxylic acid mp 275°-277°, (C, H, Cl).

Workup

  1. temperatureheated under N2 at 90° for 1.5 h
  2. filtrationfiltered
  3. customdried
  4. customthe precipitate recrystallized from EtOAc

Sources & evidence

ORD record
ord-6d81034ad1fb49a0888a8d56a45a363e
Source dataset
uspto-grants-1989_02
Patent number
US04803221

Reaction notes

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