Ammonia → HCID 70448823, compound

HRID 2412958Notes

Reaction equation

HRID 2412958 reaction equation
[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12]2)=[CH:7][CH:6]=1.[NH3:23].CO.C(Cl)(Cl)[Cl:27]>>[ClH:27].[NH2:23][CH2:22][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:21])[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 99480817-(2,3-Epoxypropoxy)flavoneHCID 21584188Chloroform methanol

Product 1

HCID 70448823HCID 70448823, compound

Procedure

7-(2,3-Epoxypropoxy)flavone (13.3 g, 0.045 mol) in a presurre bottle was treated with a methanolic solution (90 ml) containing 1.87 g of ammonia (0.11 mol). The bottle was sealed and the suspension was heated at 50° for 12 hrs. A tlc (15% MeOH/CHCl3) indicated that the starting material was gone, and the reaction mixture was cooled and filtered. The solid (5.32 g) thus obtained was shown by tlc to be a byproduct, m.p. 209°-12°. The filtrate, upon evaporation, afforded 7.0 g of a yellow solid, m.p. 121°-27°, which was purified by high pressure liquid chromatography to give 1.85 g of yellow powder, m.p. 154°-56°. (13% yield). The hydrochloride salt was prepared and recrystallized from MeOH, m.p. 191°-2°.

Workup

  1. customThe bottle was sealed
  2. temperaturethe suspension was heated at 50° for 12 hrs
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fe6e16941dc64bb08e6325619772c2bb
Source dataset
uspto-grants-1985_01
Patent number
US04495198

Reaction notes

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