4-Nitrobenzoic Acid → 4-Nitroprocainamide

HRID 641059Notes

Reaction equation

HRID 641059 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.ClCCl>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:8](=[O:10])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[CH3:14]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 60993N,N-DiethylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 165724-Nitroprocainamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-nitrobenzoic acid (2.00 g, 11.9 mmol), N,N-diethylethylene diamine (1.53 g, 13.16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.74 g, 14.35 mmol), and 1-hydroxybenzotriazole hydrate (2.19 g, 14.35 mmol) in 15 mL DMF was stirred at room temperature for 4 hours. The mixture was diluted with dichloromethane (100 mL) and washed with aqueous saturated sodium bicarbonate solution (50 mL). The aqueous layer was re-extracted with dichloromethane (2×50 mL) and the combined organic solutions were dried (Na2SO4), filtered and evaporated under reduced pressure. The crude mixture was purified on silica gel column to provide N-(2-(diethylamino)-ethyl)-4-nitrobenzamide as an amber colored oil (2.2 g 69%).

Workup

  1. washwashed with aqueous saturated sodium bicarbonate solution (50 mL)
  2. extractionThe aqueous layer was re-extracted with dichloromethane (2×50 mL)
  3. dry with materialthe combined organic solutions were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude mixture was purified on silica gel column

Sources & evidence

ORD record
ord-fe6e1669a2c4419988f5ea3b34bad979
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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