Ethylamine → 7-(3-Ethylamino-2-hydroxypropoxy) flavone hydrochloride

HRID 2412956Notes

Reaction equation

HRID 2412956 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.[CH2:23]([NH2:25])[CH3:24].[ClH:26].CCO>CO>[ClH:26].[CH2:23]([NH:25][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)[CH3:24]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 99480817-(2,3-Epoxypropoxy)flavoneHCID 21887872Ethanol hydrochloride

Product 1

HCID 704497857-(3-Ethylamino-2-hydroxypropoxy) flavone hydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to Method B, the title compound was synthesized from the reaction of 7-(2,3-epoxypropoxy) flavone and 70% aqueous ethylamine followed by treatment with HCl/EtOH, as white prisms, m.p. 244°-46° (MeOH) in 36% yield. The free base was obtained after column purification as white crystals, m.p. 164°-65° (MeOH/ehter), yield 39%.

Workup

  1. customThe free base was obtained
  2. customafter column purification as white crystals, m.p. 164°-65° (MeOH/ehter), yield 39%

Sources & evidence

ORD record
ord-11cd8dc126ad42eb8dcdf99cea5699ef
Source dataset
uspto-grants-1985_01
Patent number
US04495198

Reaction notes

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