Formaldehyde → HCID 53250974, compound

HRID 1190911Notes

Reaction equation

HRID 1190911 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:20]=O.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CCO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[C:14]([CH2:22][N:23]4[CH2:28][CH2:27][N:26]([CH3:20])[CH2:25][CH2:24]4)=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 15654508HCID 15654508, compound

Product 1

HCID 53250974HCID 53250974, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[(7-chloroquinolin-4-yl)amino]phenol (0.20 g, 0.74 mmol), formaldehyde 37% (62 μL, 1.1 eq), and N-methylpiperazine (90 μL, 1.1 eq) was dissolved in 1 mL of EtOH. The mixture was refluxed overnight, evaporated and purified by flash chromatography (DCM/MeOH/NH4OH 7.5:2.5:0.2) to yield expected compound as a pale yellow oil (42 mg, 15% yield). LC-MS: m/z (ESI) 383.3-385.3 [M+H]+

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customevaporated
  3. custompurified by flash chromatography (DCM/MeOH/NH4OH 7.5:2.5:0.2)

Sources & evidence

ORD record
ord-0a522bdd3c574e858e4c5946324ec734
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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