Methanesulfonic Acid → HCID 118323965, compound

HRID 1778213Notes

Reaction equation

HRID 1778213 reaction equation
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:20][C:21]1[CH:41]=[CH:40][C:24]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:39])[CH2:35][C:36]([OH:38])=O)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CC(C)=O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([C:27]2[CH:28]=[C:29]3[C:30](=[CH:31][CH:32]=2)[NH:33][C:34](=[O:39])[CH:35]=[C:36]3[OH:38])=[O:26])=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 118324065HCID 118324065, compound

Product 1

HCID 118323965HCID 118323965, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A 2-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, and a nitrogen inlet/outlet adapter was charged with CH3SO2OH (236.0 mL, 3.60 mol), P2O5 (34.6 g, 241.1 mmol) was added and the mixture was vigorously stirred at 80° C. for 90 min. Solid 3-((4-(4-chlorobenzoyl)phenyl)amino)-3-oxopropanoic acid (111.0 g, 321.4 mmol) was added portionwise over 3 min at 80° C., and the resulting mixture was stirred at 80° C. for 2 h. The hot mixture was poured slowly into ice-water (5 L) and vigorously agitated for 1 h. The resulting solid was collected by filtration, washed with deionized water (2 L×2), and dried by air-suction for 20 h to yield a slightly yellowish solid. The solid was suspended in acetone (990 mL) at 53° C. and sonicated for 30 min. The resulting yellowish slurry was stirred at 20° C. for 10 min. The solid was collected by filtration, washed with acetone (50 mL), dried by air-suction for 1 h and then under high vacuum (22 mmHg) at 60° C. for 20 h to yield 6-(4-chlorobenzoyl)-4-hydroxyquinolin-2(1H)-one as a light beige-yellowish solid. Elemental analysis: Calculated for C16H10ClNO5+0.1H2O+0.21CH3COCH3; MW=313.72. Theoretical: C, 63.67; H, 3.68; Cl, 11.30; N, 4.46; % H2O, 0.60; Measured: C, 63.58; H, 3.23; Cl, 11.53; N, 4.64; % H2O, 0.53

Workup

  1. customA 2-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, and a nitrogen inlet/outlet adapter
  2. additionwas added
  3. stirringthe resulting mixture was stirred at 80° C. for 2 h
  4. stirringvigorously agitated for 1 h
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with deionized water (2 L×2)
  7. customdried by air-suction for 20 h
  8. customto yield a slightly yellowish solid
  9. customsonicated for 30 min
  10. stirringThe resulting yellowish slurry was stirred at 20° C. for 10 min
  11. filtrationThe solid was collected by filtration
  12. washwashed with acetone (50 mL)
  13. customdried by air-suction for 1 h

Sources & evidence

ORD record
ord-a043aae5d34341a88c46618e3e7cba81
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…