HCID 5328852, compound → HCID 135670822, compound

HRID 379162Notes

Reaction equation

HRID 379162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21]C)=[C:16]([O:19]C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])=[C:4]([F:25])[CH:3]=1.Cl.N1C=CC=CC=1>[OH-].[NH4+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])=[C:4]([F:25])[CH:3]=1

Participants

4

Reactant 2

HCID 5328852HCID 5328852, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 135670822HCID 135670822, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
215 °C

Procedure

A mixture of 0.358 g of 4-(4-chloro-2-fluoro-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile and 3 g of pyridine hydrochloride was stirred under nitrogen at 210-220° C. for 20 minutes. The mixture was cooled and added to 50 ml of 3% ammonium hydroxide solution. The product was collected, washed with water, and dried to give 0.302 g of 4-(4-chloro-2-fluoro-phenylamino)-6,7-dihydroxy-quinoline-3-carbonitrile as a solid, mp 270-272° C.; mass spectrum (EI, m/e): M 329.0363.

Workup

  1. temperatureThe mixture was cooled
  2. customThe product was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e5516bbad25c48ba8d72546be5f26212
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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