Ammonia → HCID 21827056, compound

HRID 1669172Notes

Reaction equation

HRID 1669172 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][O:11]2)=[CH:6][C:5]=1[NH:14]C(=O)C)([O-:3])=[O:2].[CH]Cl.N>CCO>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][O:11]2)=[CH:6][C:5]=1[NH2:14])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6432229CID 6432229HCID 21827064HCID 21827064, compound

Product 1

HCID 21827056HCID 21827056, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of acetamide 232 (2.49 g, 10.5 mmol) and cHCl (10 mL) in EtOH (50 mL) was heated at reflux temperature for 16 h. The solution was cooled, carefully neutralized with aqueous NH3 solution, extracted with EtOAc (2×50 mL), the combined organic fraction dried and the solvent evaporated to give nitroaniline 238 (2.05 g, 100%) as an orange solid: mp (EtOAc) 145-148° C. [lit. (Brancaccio, G.; Lotteiri, G.; Viterbo, R. J. Het. Chem. 1973, 10, 623-629) mp (H2O) 139-140° C.]; 1H NMR δ 7.54 (s, 1H, H-8), 6.50 (s, 1H, H-5), 5.62 (br s, 2H, NH2), 4.14 (br t, J=5.2 Hz, 2H, H-2), 2.77 (br t, J=6.5 Hz, 2H, H-4), 1.95-2.02 (m, 2H, H-3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 h
  3. temperatureThe solution was cooled
  4. extractionextracted with EtOAc (2×50 mL)
  5. customthe combined organic fraction dried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d2a4ad32020f4689bbbbcf8323148d75
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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