Phosphorus oxychloride → HCID 86683003, compound

HRID 1497168Notes

Reaction equation

HRID 1497168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13](O)=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P(Cl)(Cl)([Cl:24])=O.[C:27]([O:31][CH2:32][CH:33]1[C:45]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2)(=[O:30])[NH:28][NH2:29]>O>[CH:35]1[C:34]2[CH:33]([CH2:32][O:31][C:27]([NH:28][NH:29][C:13]([C:6]3[C:7]([Cl:24])=[N:8][C:9]4[C:4]([C:5]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=4)=[O:14])=[O:30])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]=2[CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 1618839-Fluorenylmethyl carbazateHCID 620332HCID 620332, compound

Product 1

HCID 86683003HCID 86683003, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (100 mg, 334 μmol, Eq: 1.00) and phosphorus oxychloride (3.29 g, 2 ml, 21.5 mmol, Eq: 64.3) was heated to 120° C. for 3 h. The reaction mixture was evaporated to dryness and the remaining residue was co-evaporated with toluene (2×). The residue was dissolved in DCM (1 ml) and 9-fluorenylmethyl carbazate (127 mg, 500 μmol, Eq: 1.5) was added. The reaction mixture was stirred at RT for 4 h. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 9:1) to afford the title compound as off-white solid (102 mg). MS (ESI): 554.1 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in DCM (1 ml)
  3. extractionthe mixture was extracted with ethyl acetate (3×)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. customThe remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 9:1)

Sources & evidence

ORD record
ord-49b2b19994ca4eabb0b9933e90fcb256
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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