Ammonia → 2,4,6-Cycloheptatrien-1-one, 2-amino-7-bromo-

HRID 2052376Notes

Reaction equation

HRID 2052376 reaction equation
[Br:1][C:2]1[C:8](=[O:9])[C:7](OC)=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:12]>CO>[NH2:12][C:7]1[C:8](=[O:9])[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5711302-Bromo-7-methoxytropone

Product 1

HCID 373462,4,6-Cycloheptatrien-1-one, 2-amino-7-bromo-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-bromo-2-methoxy-2,4,6-cycloheptatrien-1-one [1.0 g, described by T. Nozol et al., Proc. Japan Acad., 27, 556-60 (1951), (CA 46, 7560c)] in methanol (30 ml) is cooled to -20° C. and saturated with gaseous ammonia. The reaction mixture is heated in a pressure bottle at 80° C. for four hours and cooled to -70° C. The bottle is opened and the solvent is removed under reduced pressure. The residue is boiled with ethyl acetate and the ethyl acetate extract is evaporated to give 2-amino-7-bromo-2,4,6-cycloheptatrien-1-one.

Workup

  1. temperaturecooled to -70° C
  2. customthe solvent is removed under reduced pressure
  3. extractionthe ethyl acetate extract
  4. customis evaporated

Sources & evidence

ORD record
ord-40620e5aea5d4061bacb08c1ad20e574
Source dataset
uspto-grants-1980_01
Patent number
US04183955

Reaction notes

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