Formaldehyde → HCID 67246432, compound

HRID 1190908Notes

Reaction equation

HRID 1190908 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.C=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]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[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 121243-Hydroxyacetanilide

Product 1

HCID 67246432HCID 67246432, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-hydroxyphenyl)acetamide (0.50 g, 3.31 mmol), formaldehyde 37% (678 μL, 2.7 eq), and morpholine (290 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 (107 mg, 13% yield). LC-MS: m/z (ESI) 251.3 [M+H]+; 1H NMR (300 MHz, MeOH-d4) δ7.09; (d, J=1.3 Hz, 1H), 6.8-6.9; (m, 2H), 3.6-3.7; (m, 4H), 3.58; (s, 2H), 2.4-2.5; (m, 4H), 2.0; (s, 3H)

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-1d792b20dec145048342a561cf4c2ed1
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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