Hydrochloric Acid → 4-(3-Bromophenylamino)-6,7-di-n-propoxy-3-quinolinecarbonitrile

HRID 612208Notes

Reaction equation

HRID 612208 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:20])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.[C:23](=O)([O-])[O-].[K+].[K+].I[CH2:30][CH2:31][CH3:32].Cl.C(O[CH2:38][CH3:39])(=O)C>O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH2:23][CH2:38][CH3:39])=[C:16]([O:19][CH2:30][CH2:31][CH3:32])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 1354028484-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

Product 1

HCID 224667444-(3-Bromophenylamino)-6,7-di-n-propoxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of 4(3-bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile (1.07 g, 3.0 mmol), potassium carbonate (1.66 g, 12.0 mmol), and 12 ml of DMF at 0° C. was added 1-iodopropane (1.17 ml, 12.0 mmol). The mixture was warmed to 25° C., stirred for 5 h, and then partioned at 0° C. with ethyl acetate and water containing HCl to give pH-8. The organic layer was separated, washed with water, dried, and concentrated. The residue was subjected to chromatography on silica gel with methylene chloride-ethyl acetate-acetic acid to give an amorphous solid; mass spectrum (electrospray, m/e) M+H 440.2, 442.2.

Workup

  1. customto give pH-8
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customto give an amorphous solid

Sources & evidence

ORD record
ord-f5a428b9ef084202a08817a289d87b84
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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