4-(2-Methyl-2-adamantyloxy)-nitrobenzene → 4-(2-Methyl-2-adamantyloxy)aniline

HRID 259361Notes

Reaction equation

HRID 259361 reaction equation
[CH3:1][C:2]1([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2

Participants

4

Reactant 1

HCID 125102684-(2-Methyl-2-adamantyloxy)-nitrobenzene

Product 1

HCID 125102854-(2-Methyl-2-adamantyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 15.0 g. (0.0522 mole) of 4-(2-methyl-2-adamantyloxy)-nitrobenzene in 150 ml. of ethyl acetate was hydrogenated over 10% Pd/C. The crude product was recrystallized from CH2Cl2 and Skellysolve B to give 8.6 g. of light tan solid, m.p. 95.6°-97.9° C.

Workup

  1. customThe crude product was recrystallized from CH2Cl2 and Skellysolve B
  2. customto give 8.6 g

Sources & evidence

ORD record
ord-716d75f563c84b19a63d45711c13af02
Source dataset
uspto-grants-1977_07
Patent number
US04036977

Reaction notes

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