Ethylamine → N-ethyl-3-hydroxy-4-nitrobenzamide

HRID 1717327Notes

Reaction equation

HRID 1717327 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.[CH2:14]([NH2:16])[CH3:15].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C1COCC1.C(N(CC)CC)C>[CH2:14]([NH:16][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([OH:1])[CH:3]=1)[CH3:15]

Participants

8

Reactant 4

HCID 6341EthylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692653-Hydroxy-4-nitrobenzoic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 21029708N-ethyl-3-hydroxy-4-nitrobenzamideYield 100%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-hydroxy-4-nitrobenzoic acid (9.16 g) in DMF (100 ml) were successively added 2M ethylamine in THF solution (30 ml), triethylamine (8.3 ml), HOBt (9.19 g) and WSC (11.5 g), and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, ethyl acetate and 1N hydrochloric acid were added to the residue and the insoluble material was filtered off. The filtrate was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a yellow solid (10.6 g, 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure, ethyl acetate and 1N hydrochloric acid
  2. additionwere added to the residue
  3. filtrationthe insoluble material was filtered off
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-28bdd81ea07c495c9cc1d93ee0cd723f
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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