Triethylsilane → HCID 22646632, compound

HRID 989057Notes

Reaction equation

HRID 989057 reaction equation
C([NH:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)(OC(C)(C)C)=O.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 18005018Carbamic acid, (4-chloro-6,7-dimethoxy-3-quinolinyl)-, 1,1-dimethylethyl ester

Product 1

HCID 22646632HCID 22646632, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-BOCamino-4-chloro-6,7-dimethoxyquinoline (18 g) was dissolved in trifluoroacetic acid (200 ml) with stirring, triethylsilane (80 ml) was then added. Stirred at room temperature for 2 hours. Evaporated. The dark red oily residue was treated with ice/water and carefully basified with 880 ammonia. The resulting red gum was scratched and stirred upon which it slowly solidified. Solid was filtered off and washed with water. Dried to give 3-amino-4-chloro-6,7-dimethoxyquinoline (7 g). On standing overnight more solid came out of the filtrate this was filtered off washed with water and dried to give 3-amino-4-chloro-6,7-dimethoxyquinoline (3.5 g) (Total yield 83%).

Workup

  1. stirringStirred at room temperature for 2 hours
  2. customEvaporated
  3. additionThe dark red oily residue was treated with ice/water
  4. stirringstirred upon which it
  5. filtrationSolid was filtered off
  6. washwashed with water
  7. customDried

Sources & evidence

ORD record
ord-6ffb435c9e0f446da585ad2ba381df24
Source dataset
uspto-grants-2003_10
Patent number
US06638945B1

Reaction notes

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