Acetic Anhydride → HCID 46203785, compound

HRID 885089Notes

Reaction equation

HRID 885089 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.O>[OH:17][C:4]1[CH:5]=[CH:6][C:7](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[C:2]([NH:1][C:18](=[O:20])[CH3:19])[CH:3]=1

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 11673048HCID 11673048, compound

Product 1

HCID 46203785HCID 46203785, compoundYield 46.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-amino-4-[(E)-2-(4-hydroxy-phenyl)vinyl]phenol (100 mg) in anhydrous THF was added 225 mg of acetic anhydride and 223 mg of Et3N. The resulting solution was stirred at rt overnight. The reaction mixture was concentrated by vacuum evaporation. The residue, which was identified as mainly desired compound by 1H-NMR, was not further purified and used directly for the next step. The crude mixture from the previous reaction was dissolved in 30 mL of methanol. K2CO3 (197 mg, ˜12 eq.) was added as well as 20 mL of H2O. The resulting solution was vigorously stirred at rt for 1 h. All volatile solvents were evaporated and the residue was loaded on a silica gel column with 5% MeOH/dichloromethane as eluent to give N-{5-hydroxy-2-[(E)-2-(4-hydroxyphenyl)vinyl]phenyl}-acetamide (55 mg, 46.4% in two steps). MS (ES) m/z: 270.14 (M+1); Mp. 227-229° C.

Workup

  1. concentrationThe reaction mixture was concentrated by vacuum evaporation
  2. customwas not further purified
  3. customThe crude mixture from the previous reaction
  4. stirringThe resulting solution was vigorously stirred at rt for 1 h
  5. customAll volatile solvents were evaporated

Sources & evidence

ORD record
ord-638850767b1e4a908e0812f3b6d4372b
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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