Methanol → HCID 10926725, compound

HRID 548450Notes

Reaction equation

HRID 548450 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([O:22][CH3:23])[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:24]#[N:25])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].CO>O.C(OCC)(=O)C.[Fe]>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([O:22][CH3:23])[CH:15]=1)[N:12]=[CH:11][C:10]([C:24]#[N:25])=[C:9]2[NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 11811432HCID 11811432, compound

Product 1

HCID 10926725HCID 10926725, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.15 g (5 mmol) of 4-[(3-bromophenyl)amino]-8-methoxy-6-nitro-quinoline-3-carbonitrile, 1.95 g (37.5 mmol) of ammonium chloride, and 1.26 g (22.5 mmol) iron was stirred at reflux in 40 ml of water and 40 ml of methanol for 3 hours. The mixture was diluted with 500 ml of hot ethyl acetate and the hot mixture was filtered. The filtration was washed with saturated sodium chloride solution and then the organic layer was dried over sodium sulfate. The solution was concentrated and 0.43 of dark yellow solid was collected: mass spectrum (electrospray, m/e): M+H 368.9 and 370.9.

Workup

  1. filtrationthe hot mixture was filtered
  2. filtrationThe filtration
  3. washwas washed with saturated sodium chloride solution
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationThe solution was concentrated
  6. custom0.43 of dark yellow solid was collected

Sources & evidence

ORD record
ord-82e96d050a2e41e88dd344423484403e
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

Loading…