Potassium Carbonate → HCID 67288333, compound

HRID 403653Notes

Reaction equation

HRID 403653 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1O)=[CH:10][C:9]([NH:14][C:15](=[O:17])[CH3:16])=[C:8]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:7]=2)#[N:2].P(Cl)(Cl)([Cl:25])=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:25][C:12]1[C:11]2[C:6](=[CH:7][C:8]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:9]([NH:14][C:15](=[O:17])[CH3:16])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 178496074HCID 178496074, compound

Product 1

HCID 67288333HCID 67288333, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

A stirred mixture of N-(3-cyano-4-hydroxy-7-(2-methoxyethoxy)quinolin-6-yl)acetamide (8.8 g, 0.029 mol, 1.00 equiv) in phosphorus oxychloride (70 mL, 0.765 mol, 26.4 equiv) was heated to 80-85° C. for 4 hours. The reaction mixture was cooled and filtrated. The filtrates were added to a cooled (0-10° C.) solution of potassium carbonate (270 g, 1.95 mol) in 470 ml water. The resulting yellow mixture was stirred for at least 12 hours. The mixture was filtered and washed with hot water. The collected solids were dried to give product 6.5 g. MS (ESI) m/z: 319 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltrated
  3. additionThe filtrates were added to
  4. filtrationThe mixture was filtered
  5. washwashed with hot water
  6. customThe collected solids were dried

Sources & evidence

ORD record
ord-320d6dee30604f229caceab0a66068b6
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

Loading…