Hydrazine hydrate (1:1) → HCID 53437222, compound

HRID 1873939Notes

Reaction equation

HRID 1873939 reaction equation
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([N:8]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:36])([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:30])=[CH:25][CH:24]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:22])([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:8]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([CH3:36])([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:30])=[CH:27][CH:28]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:22])([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:16])=[CH:11][CH:10]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58058451HCID 58058451, compound

Product 1

HCID 53437222HCID 53437222, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Next, 13.60 mmol of 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline, 0.22 of 10% Pd/C, and 150 ml of ethanol were added into a bottle. Next, the mixture was heated to reflux, and 7 ml of hydrazine monohydrate was added slowly to the mixture from a dropping funnel over a period of 1 hrs under dry nitrogen. After a further 12 hrs of reflux, the mixture solution was filtered to remove Pd/C, and the filtrate was cooled to precipitate. The crude product was collected by filtration and recrystallization from ethanol to afford 4-Amino-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline as a white crystal with a yield of 80%. The 4-amino-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline had a melt point of 95° C.

Workup

  1. temperatureNext, the mixture was heated
  2. temperatureto reflux
  3. temperatureAfter a further 12 hrs of reflux
  4. filtrationthe mixture solution was filtered
  5. customto remove Pd/C
  6. temperaturethe filtrate was cooled
  7. customto precipitate
  8. filtrationThe crude product was collected by filtration and recrystallization from ethanol

Sources & evidence

ORD record
ord-7cd55369d8c9450cbedb926d457954c9
Source dataset
uspto-grants-2012_11
Patent number
US08304514B2

Reaction notes

Loading…