3-Amino-1,2-propanediol → 1-(2,3-Dihydroxypropylaminocarbonyl)-3-nitro-5-(1,2-dihydroxyethyl)benzene

HRID 1280138Notes

Reaction equation

CO[C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]([OH:13])[CH2:11][OH:12])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1.[OH:18][CH:19]([CH2:22][OH:23])[CH2:20][NH2:21]>CO>[OH:18][CH:19]([CH2:22][OH:23])[CH2:20][NH:21][C:3]([C:4]1[CH:9]=[C:8]([CH:10]([OH:13])[CH2:11][OH:12])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)=[O:17]

Participants

Conditions

Temperature: 75 °C

Procedure

3-Nitro-5-(1,2-dihydroxyethyl)benzoic acid methyl ester (0.40 g, 1.69 mmol) and 2,3-dihydroxypropylamine (0.17 g, 1.86 mmol) were dissolved in methanol (2 ml) and the solution was stirred at 75° C. for 1 h. The pressure was then reduced to 200 mm Hg and stirring was continued at 95° C. for 2 h . The crude reaction mixture was purified by preparative HPLC. Yield: 0.40 g (78%).

Workup

stirringstirring
waitwas continued at 95° C. for 2 h
customThe crude reaction mixture
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-70dfc8c03c7249629b1727145628e80e
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448442B1

Reaction notes

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