HCID 86618960, compound → Deaminoimiquimod

HRID 2244563Notes

Reaction equation

HRID 2244563 reaction equation
[NH2:1][C:2]1[C:3](N)=[N:4][C:5]2[C:10]([C:11]=1CC(C)C)=[CH:9][CH:8]=[CH:7][CH:6]=2>C(O)=O>[CH2:5]([N:4]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:3]1)[CH:10]([CH3:11])[CH3:9]

Participants

3

Reactant 1

HCID 86618960HCID 86618960, compound

Product 1

HCID 11424651DeaminoimiquimodYield 196.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Conditions

Temperature
112.5 °C

Procedure

3-Amino-4-isobutyl amino quinoline (215 gm, 1.0 mole) was dissolved in formic acid (1000 ml) and further refluxed the reaction mass to 110-115° C. Reflux was maintained for 8-10 hrs. After completion of reaction excess formic acid was removed under reduced pressure and 3.5 L of water was added to the concentrated mass. This diluted mass was then basified with 30% NaOH to pH (10 to 11) at 20° C. The reaction mass was further cooled to 10° C. and stirred for further 3 hrs to obtain solid. The solid was filtered, washed with water and dried to get the title compound (221 gm, 98%) as a white solid.

Workup

  1. temperatureReflux
  2. temperaturewas maintained for 8-10 hrs
  3. customwas removed under reduced pressure and 3.5 L of water
  4. additionwas added to the concentrated mass
  5. customat 20° C
  6. temperatureThe reaction mass was further cooled to 10° C.
  7. customto obtain solid
  8. filtrationThe solid was filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-ff74a98299234235868ddfca7f0c71d6
Source dataset
uspto-grants-2010_03
Patent number
US07678912B2

Reaction notes

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