Ethylenediamine → trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol

HRID 344767Notes

Reaction equation

HRID 344767 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]3([O:15][CH:8]3[C:7]=2[CH:16]=1)O)#[N:2].[CH2:17]([NH2:20])[CH2:18][NH2:19]>C(O)C>[NH2:19][CH2:18][CH2:17][NH:20][C@@H:8]1[C:7]2[CH:16]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:12])([CH3:13])[C@H:9]1[OH:15]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 190215466-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran-3-ol

Product 1

HCID 15680853trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-olYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran-3-ol (0.927g) and ethylenediamine (2.78g) was heated under reflux in ethanol (70 ml) for 16 h. The solvent was evaporated in vacuo and the residue column chromatographed (Kieselgel 60, gradient elution: 0-9% 880 ammonia-methanol) giving the title compound (0.868g) as a foam.

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated in vacuo
  3. customthe residue column chromatographed
  4. wash(Kieselgel 60, gradient elution: 0-9% 880 ammonia-methanol)

Sources & evidence

ORD record
ord-f8017f5b33e6448ba151c0068b0562ae
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

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