Aniline → HCID 178434107, compound

HRID 2095198Notes

Reaction equation

HRID 2095198 reaction equation
[C:1]([NH:5][C:6](=O)[C:7](=[N:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8](=O)[CH3:9])([CH3:4])([CH3:3])[CH3:2].NC1C=CC=CC=1.C(NC(=O)CC(C)=O)(C)(C)C.O.[NH2:39][NH2:40]>C(O)C>[C:1]([NH:5][C:6]1[C:7](=[N:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([CH3:9])=[N:40][N:39]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6115AnilineHCID 24654Hydrazine hydrate (1:1)HCID 257712N-tert-butyl-3-oxobutanamideHCID 178468317HCID 178468317, compound2×

Product 1

HCID 178434107HCID 178434107, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared using 100 mg (0.4 mmol) of N-tert-butyl-3-oxo-2-(phenylhydrazono)butyramide which was synthesized using aniline (1.7 mmol) and N-tert-butyl acetoacetamide (393 mg, 2.5 mmol). Hydrazine hydrate (2.3 mmol) was added to a solution of N-tert-butyl-3-oxo-2-(phenylhydrazono)butyramide in ethanol. Very little solid had formed after heating the reaction at 75° C. for 1 hour, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to ambient temperature and the solvent was evaporated. The residue was recrystallized from ethanol/water. The resulting solid was isolated by filtration and dried to yield 38 mg (43%) of the title compound as a yellow solid. 1H NMR (ppm, 200 MHz, CDCl3) δ 1.42 (s, 9H), 2.20 (s, 3H), 5.35 (br s, 1H), 6.95 (t, 1H), 7.15-7.35 (m, 4H), 9.95 (br s, 1H); IR (cm−1, KBr pellet): 3368 (w), 3197 (w), 3038 (w), 2973 (w), 2928 (w), 1631 (m), 1602 (m), 1565 (m), 1516 (s), 1498 (s), 1391 (w), 1366 (m), 1225 (m), 1187 (w), 1166 (w), 1119 (w), 1074 (w), 1059 (w), 949 (w), 895 (w), 775 (w), 748 (w), 691 (m), 561 (w); MS (m/z, ES+): 276.2 (M+18, 5%), 259.2 (M+1, 1%), 203.1 (M-55, 5%).

Workup

  1. customThe title compound was prepared
  2. customwas synthesized
  3. customVery little solid had formed
  4. temperatureafter heating
  5. customthe reaction at 75° C. for 1 hour
  6. customthe solvent was evaporated
  7. customThe residue was recrystallized from ethanol/water
  8. customThe resulting solid was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-ca29e56d92fb44e59a04ed65afbc7f99
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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