Ammonium Hydroxide → HCID 178426076, compound

HRID 986822Notes

Reaction equation

HRID 986822 reaction equation
[CH3:1][C:2]1[NH:16][C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[N:3]=1)[N:10]=[C:9]([CH3:14])[CH:8]=[C:7]3O.O=P(Cl)(Cl)[Cl:19].[NH4+].[OH-]>CN(C)C=O>[Cl:19][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]3[N:3]=[C:2]([CH3:1])[NH:16][C:5]3=2)[N:10]=[C:9]([CH3:14])[CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178428807HCID 178428807, compound

Product 1

HCID 178426076HCID 178426076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 31 g. (0.146 m.) of 2,7-dimethyl-1H-imidazo[4,5-f]quinoline-9-ol and 1336 ml. (223 g. 1455 m.) of POCl3 is added dropwise 267.2 ml. of dimethylformamide. The mixture is stirred overnight at room temperature, then poured into 1000 ml. of ice. The solution is basified to pH 8.0 using conc. NH4OH, keeping the temperature below 20° C. It is then filtered, washed with H2O and air-dried. The crude product is recrystallized from 2000 ml. of MeOH, and concentrated in vacuo to yield 338 g. m.p. 314°-330° C.

Workup

  1. additionTo a mixture of 31 g
  2. additionpoured into 1000 ml
  3. customthe temperature below 20° C
  4. filtrationIt is then filtered
  5. washwashed with H2O
  6. customair-dried
  7. customThe crude product is recrystallized from 2000 ml
  8. concentrationof MeOH, and concentrated in vacuo
  9. customto yield 338 g

Sources & evidence

ORD record
ord-69a6a9005db74c97b5d0386af3dbceed
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Reaction notes

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