Hydrazine hydrate (1:1) → HCID 178443470, compound

HRID 1612596Notes

Reaction equation

HRID 1612596 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:24])([O-])=O.O.NN>C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([C@H:10]2[CH2:11][CH2:12][C@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:15]2)[CH:7]=[CH:6][C:5]=1[OH:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178443471HCID 178443471, compound

Product 1

HCID 178443470HCID 178443470, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Step ii) In a 50 ml-three-necked flask, 1.90 g (5.70 mM) of 2-nitro-4-(trans-4-octylcyclohexyl)phenol, 0.35 g of activated carbon, 0.04 g of FeCl3.6H2O and 15 ml of ethanol were placed and heated to 55°-65° C. under stirring. To the mixture, 1.8 ml of 80% hydrazine hydrate was gradually added dropwise and heated to 70° C., followed by stirring for 20 min at 70° C. After the reaction, the reaction mixture was filtered under heating to remove the activated carbon and the filtrate was cooled to room temperature to precipitate a crystal. The crystal was recovered by filtration and recrystallized from ethanol to obtain 1.49 g of 2-amino-4-(trans-4-octylcyclohexyl)phenol (yield: 86.2%).

Workup

  1. temperatureheated to 55°-65° C.
  2. stirringby stirring for 20 min at 70° C
  3. customAfter the reaction
  4. filtrationthe reaction mixture was filtered
  5. temperatureunder heating
  6. customto remove the activated carbon
  7. temperaturethe filtrate was cooled to room temperature
  8. customto precipitate a crystal
  9. filtrationThe crystal was recovered by filtration
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-04b43b6995224409b5d75125eb4c68b6
Source dataset
uspto-grants-1993_03
Patent number
US05190690

Reaction notes

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