Salicylic Acid → 3-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

HRID 1955671Notes

Reaction equation

HRID 1955671 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH2:11])[CH:3]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23]>CN1CCCC1=O.C(OCC)(=O)C>[C:20]([OH:29])(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23].[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([NH:11][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 338Salicylic AcidHCID 818524-Chloropyridine hydrochlorideHCID 9964198N-Amino-3-chloro-1H-indole

Product 1

HCID 700281183-Chloro-N-(4-pyridinyl)-1H-indol-1-amine salicylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of crude 3-chloro-1H-indol-1-amine (65.5 g) and 4-chloropyridine hydrochloride (45 g) in 1-methyl-2-pyrrolidinone (250 ml) was stirred at 60° C. for eight hours. The cooled reaction mixture was quenched into 5% aqueous sodium hydroxide, extracted into toluene, dried and concentrated to give an oil. A portion of this oil was dissolved in ethyl acetate. Salicylic acid (1.2 eq) was added to precipitate the salt. The solid was collected at room temperature and dried. This solid was recrystallized with a charcoal treatment from methanol and oven dried (75° C., house vacuum) overnight to yield 10.9 g of the title compound as a solid, m.p. 185°-186° C. (dec.).

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched into 5% aqueous sodium hydroxide
  3. extractionextracted into toluene
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil
  7. customto precipitate the salt
  8. customThe solid was collected at room temperature
  9. customdried
  10. customThis solid was recrystallized with a charcoal treatment from methanol and oven
  11. customdried (75° C., house vacuum) overnight

Sources & evidence

ORD record
ord-9c978422951b49fc94b95ff9711b848a
Source dataset
uspto-grants-1998_07
Patent number
US05776955

Reaction notes

Loading…