Hydrazine hydrate (1:1) → HCID 397907, compound

HRID 902586Notes

Reaction equation

HRID 902586 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[N+:42]([O-])=O)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[C:31]([OH:38])[CH:30]=4)=[CH:24][CH:23]=3)[CH:19]3[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:21][CH:13]2[CH2:14]4)[CH2:18]3)=[CH:8][CH:7]=1.O.NN>[Pd].C(O)C>[NH2:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][C:25]2[CH:24]=[CH:23][C:22]([C:12]3([C:9]4[CH:10]=[CH:11][C:6]([O:5][C:4]5[CH:39]=[CH:40][C:41]([NH2:42])=[C:2]([OH:1])[CH:3]=5)=[CH:7][CH:8]=4)[CH:13]4[CH2:21][CH:17]5[CH2:16][CH:15]([CH2:20][CH:19]3[CH2:18]5)[CH2:14]4)=[CH:27][CH:26]=2)=[CH:30][C:31]=1[OH:38]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11953114HCID 11953114, compound

Product 1

HCID 397907HCID 397907, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2,2-bis(4-(3-hydroxy-4-nitrophenoxy)phenyl)adamantane (3.00 g, 5.05 mmol), 10% Pd/C (0.06 g) and ethanol (60 mL) were heated to reflux. Then, 20 mL of hydrazine hydrate was added dropwise into the suspension solution over a period of 1 hour. After the mixture was refluexed for another 24 h. The reaction solution was then filtered to remove Pd/C. The crude product was recrystallized from ethanol to give 1.81 g (67.1%) of 2,2-bis(4-(4-amino-3-hydroxyphenoxy)phenyl)adamantane. mp>160° C. (decompose); IR (KBr): 3415, 3298, 2912 cm−1, MS (EI) m/z 534 (M+, 100); Anal. Calcd. for C34H34N2O4: C, 76.40; H, 6.36; N, 5.24. Found: C, 76.21; H, 6.45; N, 5.22.

Workup

  1. temperaturewere heated to reflux
  2. filtrationThe reaction solution was then filtered
  3. customto remove Pd/C
  4. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-cc0098621a104dcc830fdc86f24ea222
Source dataset
uspto-grants-2008_04
Patent number
US07365231B2

Reaction notes

Loading…