Hydrochloric Acid → 4-Amino-8-(2,6-dichlorobenzoylamino)quinoline

HRID 613576Notes

Reaction equation

[Cl:1][C:2]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[N:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:17][C:12]1[C:11]2[C:16](=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([Cl:1])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:41])[CH:8]=[CH:9][CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-4-[(triphenylphosphoranylidene)amino]quinoline (310 mg), 6N hydrochloric acid (5 ml) and acetic acid (5 ml) was heated for 3 hours at 130° C. After cooling, the mixture was neutralized with 6N sodium hydroxide solution, and the insoluble material was collected by filtration. The residue was recrystallized from ethyl acetate to give 4-amino-8-(2,6-dichlorobenzoylamino)quinoline (174 mg).

Workup

temperatureAfter cooling
filtrationthe insoluble material was collected by filtration
customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-d2585a3889fd4f3a9d430e42359e0a3e
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

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