N,N-Dimethylethylenediamine → 5-Amino-2-(2-(dimethylamino)ethyl)-4-methyl-6-nitroisoindoline-1,3-dione

HRID 69355Notes

Reaction equation

HRID 69355 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:14]([O:16]C)=O)[C:3]=1[CH3:18].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44][NH2:45]>C1COCC1.C(N(CC)CC)C>[NH2:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6](=[O:8])[N:45]([CH2:44][CH2:43][N:42]([CH3:46])[CH3:41])[C:14]2=[O:16]

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 597616804-Amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid

Product 1

HCID 666867265-Amino-2-(2-(dimethylamino)ethyl)-4-methyl-6-nitroisoindoline-1,3-dioneYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-amino-2-(methoxycarbonyl)-3-methyl-5-nitrobenzoic acid (0.43 g, 1.69 mmol), EDCI hydrochloride (0.36 g, 1.86 mmol), and HOBt (0.23 g, 1.69 mmol) in 22 mL of anhydrous THF was added 1.18 mL of triethylamine and stirred for 10 min at rt under an argon atmosphere. N1,N1-dimethylethane-1,2-diamine (0.16 g, 1.86 mmol) was added into above mixture and the reaction mixture was heated at reflux for 14 h under an argon atmosphere. Product was purified by a silica gel column using methylene chloride and methanol (9:1 v/v) as eluent to afford 0.44 g (90%) of the designed compound as yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.21 (s, ArH), 8.12 (br s, 2H, NH2), 3.64 (t, J=6.5 Hz, 2H, CH2), 2.57 (s, 3H, CH3), 2.45 (t, J=6.5 Hz, 2H, CH2), 2.15 (S, 6H, 2×CH3); Mass (ESI, positive) m/z 293.0 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 14 h under an argon atmosphere
  3. customProduct was purified by a silica gel column

Sources & evidence

ORD record
ord-cf56ec4ff0b44394b04bf9fcb1e8afeb
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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