Propylenediamine → HCID 67263825, compound

HRID 1040727Notes

Reaction equation

HRID 1040727 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1F.[NH2:15][CH2:16][CH:17]([NH2:19])[CH3:18].C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH3:18][CH:17]1[CH2:16][NH:15][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:4]=2[C:3](=[O:14])[NH:19]1

Participants

5

Reactant 3

HCID 6567PropylenediamineHCID 81531DiisopropylethylamineHCID 597752Methyl 2-fluoro-6-nitrobenzoate

Product 1

HCID 67263825HCID 67263825, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-fluoro-6-nitrobenzoic acid methyl ester (500 mg, 2.51 mmol) in 1,4-dioxane (3 mL) was treated with 1,2-diaminopropane (0.186 mL, 2.51 mmol) and diisopropylethylamine (0.874 mL, 2.51 mmol). The reaction was irradiated at 140° C. for 20 minutes. The reaction mixture was then reduced en vacuo and purified by flash column chromatography (0% ethyl acetate/hexanes—100% ethyl acetate/hexanes) to afford 370 mg of 3-Methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one and 2-Methyl-6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (mixture of regioisomers) as a yellow oil.

Workup

  1. customThe reaction was irradiated at 140° C. for 20 minutes
  2. custompurified by flash column chromatography (0% ethyl acetate/hexanes—100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-817decd9128e4cbc8b664f08149b60eb
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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