Sodium Azide → 2-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

HRID 398266Notes

Reaction equation

HRID 398266 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[OH:8])=[O:4].[N-:19]=[N+:20]=[N-:21].[Na+]>>[N:19]([CH2:2][C:3]([NH:5][CH2:6][CH:7]([C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[OH:8])=[O:4])=[N+:20]=[N-:21]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 113578062-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Product 1

HCID 115943302-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Procedure

The synthesis of Midodrine HCl consists of reacting the key intermediate (2) with chloroacetyl chloride to afford 2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (3). The reaction of (3) with sodium azide will provide 2-azido-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide (4) which is subsequently subjected to hydrogenation to afford Midodrine base (6).

Sources & evidence

ORD record
ord-be5fb5e3691e4d648c52f8812a3a70c2
Source dataset
uspto-grants-2003_08
Patent number
US06610886B2

Reaction notes

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