Ammonium Hydroxide → trans-4-amino-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran

HRID 1030209Notes

Reaction equation

HRID 1030209 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:17])([CH3:16])[O:4][C:5]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:6]=12.[OH-].[NH4+:19]>C(O)C>[NH2:19][C@@H:7]1[C:6]2[CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][C:3]([CH3:17])([CH3:16])[C@H:2]1[OH:1]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 142103893,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 67793093trans-4-amino-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran (4.0 g), ammonium hydroxide (containing ca. 28% ammonia, 40 ml), and ethanol (20 ml) was stirred at room temperature for 72 hours. The reaction mixture was concentrated, added to diisopropyl ether, and pulverized to give trans-4-amino-3,4-dihydro-3-hydroxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran (4.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded to diisopropyl ether

Sources & evidence

ORD record
ord-5e9a3687dc6645a7b831b784f42803e1
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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