Water → 3-(1-Adamantyl)-4-methoxyaniline

HRID 1756447Notes

Reaction equation

HRID 1756447 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:21]=[CH:22][C:23]=3[O:24][CH3:25])[NH:14]C(=O)C(F)(F)F)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[K+]>CO>[C:1]12([C:11]3[CH:12]=[C:13]([CH:21]=[CH:22][C:23]=3[O:24][CH3:25])[NH2:14])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 190682803-(1-adamantyl)4-methoxy-N-(trifluoroacetyl)aniline

Product 1

HCID 80271163-(1-Adamantyl)-4-methoxyaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

11.03 g (31.2 mmol) of 3-(1-adamantyl)4-methoxy -N-(trifluoroacetyl)aniline dissolved in 40 ml of methanol and 160 ml of water are treated with 7.12 g (51.5 mmol) of potassium hydroxide. The reaction medium is heated to 50° C. for 20 hours and then 80° C. for 18 hours. After evaporation to dryness, the residue is taken up with ethyl ether, the insoluble matter is filtered off and the filtrate is dried over magnesiumsulphate and evaporated. The solid is washed in hexane to yield, after drying, 7.44 g (93%) of 3-(1-adamantyl)-4-methoxyaniline, melting point 140°-141° C.

Workup

  1. customAfter evaporation to dryness
  2. filtrationthe insoluble matter is filtered off
  3. dry with materialthe filtrate is dried over magnesiumsulphate
  4. customevaporated
  5. washThe solid is washed in hexane
  6. customto yield
  7. customafter drying

Sources & evidence

ORD record
ord-2d80fc7d1b8149999c9678d4fdcc4f8b
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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