Formaldehyde → HCID 11322268, compound

HRID 1190905Notes

Reaction equation

HRID 1190905 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:12]=O.O.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>CCO>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[CH2:12][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 121243-HydroxyacetanilideHCID 31268Pyrrolidine

Product 1

HCID 11322268HCID 11322268, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-hydroxyphenyl)acetamide (0.50 g, 3.31 mmol), formaldehyde 37% in water (678 μL, 2.7 eq), and pyrrolidine (276 μL, 1 eq) were dissolved in 10 mL of EtOH. The reaction mixture was refluxed overnight, evaporated and purified by flash chromatography (DCM/MeOH/NH4OH 9.6:0.4:0.1) to yield expected compound as a pale yellow oil (224 mg, 29% yield). LC-MS: m/z (ESI) 235.13 [M+H]+

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customevaporated
  3. custompurified by flash chromatography (DCM/MeOH/NH4OH 9.6:0.4:0.1)

Sources & evidence

ORD record
ord-8773ddb36c8e4f248fdf0541d2a85a21
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…