Gallic Acid → 3,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamide

HRID 393841

Reaction equation

HRID 393841 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.Cl.[N+:14]([C:17]1(OCC)[CH:22]=[CH:21][C:20](N)=[CH:19][CH2:18]1)([O-:16])=[O:15].Cl.C[N:29](C)[CH2:30][CH2:31]CN=C=NCC.C(N(CC)CC)C>ClCCl.O.CN(C=O)C>[OH:9][C:8]1[CH:10]=[C:2]([CH:3]=[C:4]([OH:5])[C:6]=1[OH:7])[C:1]([NH:29][CH2:30][CH2:31][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=1)=[O:12]

Participants

8

Reactant 4

HCID 370Gallic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690034264-Nitrophenetylamine hydrochloride

Product 1

HCID 219187493,4,5-trihydroxy-N-[2-(4-nitrophenyl)ethyl]-benzamideYield 42%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

2 g (11.5 mmoles) of gallic acid, 2.5 g (11.5 mmoles) of 4-nitrophenetylamine hydrochloride, 1.8 g (11.5 mmoles) of hydrated 1-hydroxybenzotriazole, 2.25 g (11.5 mmoles) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.3 ml (23 mmoles) of triethylamine are introduced into a 100 ml flask containing 30 ml of anhydrous DMF. The orange-coloured solution obtained is agitated at 20° C. for 20 hours and diluted in a mixture of dichloromethane (50 ml) and water (30 ml). After decanting, the organic phase is washed with a molar solution of hydrochloric acid (20 ml) and with water (3×20 ml) until neutrality is achieved. After drying the organic phase over magnesium sulphate, followed by filtration and concentration under vacuum, the residue is purified on a silica gel column (eluant: dichloromethane/methanol: 9/1). The expected product is obtained in the form of a colourless oil with a yield of 42% (1.57 g).

Workup

  1. customThe orange-coloured solution obtained
  2. customAfter decanting
  3. washthe organic phase is washed with a molar solution of hydrochloric acid (20 ml) and with water (3×20 ml) until neutrality
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. filtrationfollowed by filtration and concentration under vacuum
  6. customthe residue is purified on a silica gel column (eluant: dichloromethane/methanol: 9/1)

Sources & evidence

ORD record
ord-3d2b27f7903649bf8c4258caa2a66e02
Source dataset
uspto-grants-2004_10
Patent number
US06809088B2

Linked notes

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