Phosphorus oxide (P4O10) → HCID 118324013, compound

HRID 1778254Notes

Reaction equation

HRID 1778254 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:23])[CH:19]=[CH:18][C:17]=1[NH:31][C:32]([CH2:34][C:35](O)=[O:36])=[O:33]>[Cl-].[Na+]>[Br:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)=[O:23])[CH:19]=[C:18]2[C:17]=1[NH:31][C:32](=[O:33])[CH:34]=[C:35]2[OH:36]

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 118324010HCID 118324010, compound

Product 1

HCID 118324013HCID 118324013, compound

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 250-mL 3-necked round-bottom flask, was placed P2O5 (8.95 g, 63.03 mmol, 1.00 equip), and MSA (80.55 g). The resulting solution was stirred for 1 h at 80° C. and then the temperature was raised to 99° C. To the resulting mixture was then added 2-([2-bromo-4-[(4-chlorophenyl)carbonyl]phenyl]carbamoyl) acetic acid (25 g, 63.03 mmol, 1.00 equip) in several batches. The resulting solution was stirred for 3 h at 99° C. The resulting solution was cooled to room temperature and added dropwise into saturated sodium chloride (500 mL). The solids were collected by filtration and then dissolved in ethyl acetate (200 mL). And the un-dissolved solids were collected by filtration to yield 8-bromo-6-[(4-chlorophenyl)carbonyl]-4-hydroxy-1,2-dihydroquinolin-2-one as a yellow solid. The filtrate was concentrated under vacuum and was applied onto a silica gel column with ethyl acetate first and then dichloromethane/methanol (8:2) to yield additional 8-bromo-6-[(4-chlorophenyl)carbonyl]-4-hydroxy-1,2-dihydroquinolin-2-one as a yellow solid. LCMS (ES, m/z) 378 [M+H]+

Workup

  1. customInto a 250-mL 3-necked round-bottom flask, was placed
  2. temperaturethe temperature was raised to 99° C
  3. stirringThe resulting solution was stirred for 3 h at 99° C
  4. temperatureThe resulting solution was cooled to room temperature
  5. filtrationThe solids were collected by filtration
  6. dissolutiondissolved in ethyl acetate (200 mL)
  7. filtrationAnd the un-dissolved solids were collected by filtration

Sources & evidence

ORD record
ord-23608c1b10a3418f9a14eedce983c3e6
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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