Ethyl formate → N-Formyl-p-(1-adamantyloxy)aniline

HRID 66091Notes

Reaction equation

HRID 66091 reaction equation
[C:1]12([O:11][C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:19](OCC)=[O:20]>>[CH:19]([NH:16][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:1]23[CH2:8][CH:7]4[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]4)[CH2:2]2)[CH2:10]3)=[CH:18][CH:17]=1)=[O:20]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 72894774-(1-Adamantyloxy)aniline

Product 1

HCID 12510309N-Formyl-p-(1-adamantyloxy)aniline

Procedure

A suspension of 10.0 g. (0.041 mole) of p-(1-adamantyloxy)aniline in 60 ml. ethyl formate was stirred at reflux for 48 hours. The mixture was then taken to dryness and the residue recrystallized from Me2CO:cyclohexane. There was obtained 9.67 g. (87%) of the amide, N-formyl-p- (1-adamentyloxy)aniline m.p. 149°-150°.

Workup

  1. additionA suspension of 10.0 g
  2. temperatureat reflux for 48 hours
  3. customthe residue recrystallized from Me2CO
  4. customThere was obtained 9.67 g

Sources & evidence

ORD record
ord-e9be8195b9ad443788f78dcb9649addf
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Reaction notes

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