Aluminum(III) Chloride → 5-(6-Chloro-pyrimidine-4-carbonyl)-1,3-dihydro-indol-2-one

HRID 469310Notes

Reaction equation

HRID 469310 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[O:11]=[C:12]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[CH:18]2)=[N:13]1.[Cl-].[Cl-].[Cl-].[Al+3]>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:11])[CH2:20]3)=[O:9])[CH:3]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 17904787Indol-2-oneHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 581811875-(6-Chloro-pyrimidine-4-carbonyl)-1,3-dihydro-indol-2-one

Procedure

3.93 g (22.2 mmol) 6-chloropyrimidine-4-carboxylic acid chloride, 2.96 g (22.2 mmol) 2-oxoindole and 14.8 g (111 mmol) aluminium trichloride were combined and heated for 3 h to 130° C. Then the mixture was mixed with ice water and extracted twice with EtOAc. The organic phases were combined, dried and evaporated down. The residue was triturated in DIPE, suction filtered, washed and dried.

Workup

  1. temperatureheated for 3 h to 130° C
  2. extractionextracted twice with EtOAc
  3. customdried
  4. customevaporated down
  5. customThe residue was triturated in DIPE, suction
  6. filtrationfiltered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-1e386c55299543d7bb46a334762f72bd
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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