Sodium Hydroxide → HCID 13370669, compound

HRID 2412973Notes

Reaction equation

HRID 2412973 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=O)C.[OH-].[Na+]>C(O)C>[NH2:4][C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 13370668HCID 13370668, compound

Product 1

HCID 13370669HCID 13370669, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g. of 4'-acetamido-4,4"-dimethoxy-1,1':2',1"-terphenyl in 250 ml. of 2B ethanol and 30 ml. of 5N sodium hydroxide was allowed to reflux overnight. Another 30 ml. of 5N sodium hydroxide were added and the reaction was allowed to reflux an additional 24 hours. The solution was then treated with 23 ml. of hydrochloric acid and evaporated in vacuo. The residue was taken up in 500 ml. of diethyl ether and 500 ml. of ethyl acetate. The organic solution was washed with water until neutral, dried over sodium sulfate, filtered, and evaporated in vacuo. The residue was crystallized from diethyl ether to provide 6.42 g. of the desired amino intermediate, m.p. about 115°-117° C.

Workup

  1. temperatureto reflux overnight
  2. temperatureto reflux an additional 24 hours
  3. additionThe solution was then treated with 23 ml
  4. customof hydrochloric acid and evaporated in vacuo
  5. washThe organic solution was washed with water until neutral,
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was crystallized from diethyl ether
  10. customto provide 6.42 g

Sources & evidence

ORD record
ord-02901effb2d84e4aaceda7214cddfec0
Source dataset
uspto-grants-1985_01
Patent number
US04495202

Reaction notes

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