Dichloromethane → HCID 178526238, compound

HRID 1357645Notes

Reaction equation

HRID 1357645 reaction equation
FC1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]2([O:19][CH2:20][CH:21]2[CH2:23][CH2:22]2)[CH:16]([F:18])[F:17])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.[CH2:35]([Cl:37])Cl>>[Cl:37][C:35]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]([O:19][CH2:20][CH:21]4[CH2:23][CH2:22]4)([CH:16]([F:18])[F:17])[C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][N+:8]=3[O-:32]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 70297m-Chloroperbenzoic acidHCID 18187330HCID 18187330, compound

Product 1

HCID 178526238HCID 178526238, compoundYield 70%

Conditions

Temperature
23 °C

Procedure

Method FF: To a 10.0 mL round bottom equipped with a magnetic stirrer, and nitrogen inlet was added 7-fluoro-9-cyclopropylmethoxy-9-difluoromethyl-4-azaacridine (1.4 g, 4.15 mmol) and anhydrous CH2Cl2 (50 mL). MCPBA (1.23 g, 4.64 mmol) was added in portions and stirred at 23° C. for 4 h. The reaction mixture was diluted with CH2Cl2, washed with sat. NaHCO3 solution (3×100 mL), brine and dried (MgSO4). Concentration afforded a yellow residue which was purified by column chromatography (SiO2, 1% Et3N-EtOAc) to afford 1.03 g of 7-Chloro-5-cyclopropylmethoxy-5-difluoromethyl-5,10-dihydro-benzo[b][1,8]naphthyridine 1-oxide as a light green solid (mp 185-186° C., 70% yield).

Workup

  1. customMethod FF: To a 10.0 mL round bottom equipped with a magnetic stirrer, and nitrogen inlet
  2. washwashed with sat. NaHCO3 solution (3×100 mL), brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration
  5. customafforded a yellow residue which
  6. customwas purified by column chromatography (SiO2, 1% Et3N-EtOAc)

Sources & evidence

ORD record
ord-0a3ed8f34b7749ad8b5e077b85f56b02
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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