Ammonia → HCID 59691680, compound

HRID 735108Notes

Reaction equation

HRID 735108 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13]C(=O)C)=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH3:2].N>Cl>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68818446HCID 68818446, compound

Product 1

HCID 59691680HCID 59691680, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.85 g (6.26 mmol) of N-[4-(2-diethylaminoethoxy)-3-nitrophenyl]acetamide in semiconcentrated aqueous hydrochloric acid is stirred for 2 hours at 100° C., cooled to ambient temperature, made basic with ice, and concentrated aqueous ammonia and the aqueous phase is exhaustively extracted with ethyl acetate. The combined organic phases are washed with water and dried over sodium sulfate. Yield: 1.38 g (87% of theory); C12H19N3O3 (M=253.30); calc.: molecular ion peak (M+H)+: 254; found: molecular ion peak (M+H)+: 254; Rf value: 0.68 (Alox, dichloromethane/methanol (39:1)).

Workup

  1. extractionthe aqueous phase is exhaustively extracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-6d5b36d152e74baabbf55d86684a4c5b
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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