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

HRID 920482
Notes
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Reaction equation

HRID 920482 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-06e49f72f8c24786a5c1f870fae0f32c
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273055B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes