Hydrogen Bromide → HCID 14555935, compound

HRID 649113Notes

Reaction equation

HRID 649113 reaction equation
C([N:4]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[C:18]([Cl:23])[CH:17]=2)[C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][CH:6]=1)(=O)C.Br>C(O)(=O)C>[Cl:23][C:18]1[CH:17]=[C:16]2[C:21]([CH:22]=[C:13]([NH:4][C:5]3[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=3)[CH:14]=[N:15]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14555934HCID 14555934, compound

Product 1

HCID 14555935HCID 14555935, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-[N-acetyl-N-(4-methoxyphenyl)amino]-7-chloroquinoline (13.0 g), acetic acid (90 ml) and hydrobromic acid (48%, 90 ml) was heated under reflux with stirring for 5 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and dilute aqueous sodium bicarbonate. The organic layer was separated, dried over magnesium sulphate and evaporated to give 4-[N-(7-chloroquinolin-3-yl)amino]phenol as a dark yellow solid (9 g, 85%, mp 218° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and dilute aqueous sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-98e9be37b81b4b3ab5f2cbeb52c46333
Source dataset
uspto-grants-1988_04
Patent number
US04738710

Reaction notes

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