Ethanol → Ethyl 4-benzylamino-2-ethoxy-5-nitro-benzoate

HRID 578056Notes

Reaction equation

HRID 578056 reaction equation
[CH2:1]([NH:8][C:9]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([OH:26])[CH3:25].OS([O-])(=O)=O.[K+]>O>[CH2:1]([NH:8][C:9]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:26][CH2:24][CH3:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 516920Potassium bisulfateHCID 67230873Ethyl 4-benzylamino-2-fluoro-5-nitro-benzoate

Product 1

HCID 67233615Ethyl 4-benzylamino-2-ethoxy-5-nitro-benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product obtained at (655b) (15.5 g, 2.97 mmol) was combined with a mixture of potassium tert.-butylate (6.00 g, 53.5 mmol) and 400 mL ethanol, that was stirred at ambient temperature already for 15 min. After stirring for 1 h, 400 mL ethanol were added. After further 1 h of stirring, potassium tert.-butylate (500 mg, 4.46 mmol) was added. After further 1.5 h, the mixture was poured into water and acidified with KHSO4 (aq). After stirring for 20 min, the precipitate was filtered off, washed with water and dried at 55° C.

Workup

  1. stirringAfter stirring for 1 h
  2. stirringAfter further 1 h of stirring
  3. waitAfter further 1.5 h
  4. stirringAfter stirring for 20 min
  5. filtrationthe precipitate was filtered off
  6. washwashed with water
  7. customdried at 55° C.

Sources & evidence

ORD record
ord-df6e1412688b4290a9c3ca04481397d0
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

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