Dimethylformamide → HCID 178426075, compound

HRID 986821Notes

Reaction equation

HRID 986821 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:8]3=2)[N:3]=1.O=P(Cl)(Cl)[Cl:24].CN(C)C=O>CO>[Cl:24][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:8]3=2)[N:3]=[C:2]([CH3:1])[CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178428804HCID 178428804, compound

Product 1

HCID 178426075HCID 178426075, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 88 g. (0.32 m.) of 7-methyl-2-phenyl-9-imidazo[4,5-f]quinolinol (Example V D above) and 293 ml. (481 g. 3.2 m.) of POCl3 is added slowly 586 ml. of dimethylformamide. Following the completion of the addition, stirring is continued overnight at room temperature. It is then poured into 4 liters of ice. The crude product is precipitated by the addition of 1200 ml. of conc. NH4OH to pH 8.0. It is collected by filtration, washed with H2O and air-dried to give 154 g. m.p. 136°-250° C., slow decomposition. After dissolving the crude product in 5 liters of MeOH, the MeOH filtrate is concentrated to a volume of 750 ml. and chilled. The yield after oven-drying (100° C.) is 41 g. A second recrystallization from 2000 ml. of MeOH and followed by concentration to one-half its volume yields 28 g.

Workup

  1. additionTo a mixture of 88 g
  2. additionthe completion of the addition
  3. customThe crude product is precipitated by the addition of 1200 ml
  4. filtrationIt is collected by filtration
  5. washwashed with H2O
  6. customair-dried
  7. customto give 154 g
  8. concentrationthe MeOH filtrate is concentrated to a volume of 750 ml
  9. temperatureand chilled
  10. customThe yield
  11. customafter oven-drying (100° C.)
  12. customA second recrystallization from 2000 ml
  13. concentrationof MeOH and followed by concentration to one-half its volume
  14. customyields 28 g

Sources & evidence

ORD record
ord-4ebaedaca0d342499f846af9704af993
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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