Pyridine → HCID 67263677, compound

HRID 1041588Notes

Reaction equation

HRID 1041588 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]1=2.N1C=CC=CC=1.[C:23]1(=[O:37])[N:27]([CH2:28][C:29](Cl)=[O:30])[C:26](=[O:32])[C:25]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:24]12>CN(C)C1C=CN=CC=1.ClCCCl>[CH3:1][C:2]1([CH3:16])[CH2:8][CH2:7][CH2:6][N:5]([C:29](=[O:30])[CH2:28][N:27]2[C:23](=[O:37])[C:24]3[C:25](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:26]2=[O:32])[C:4]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]1=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 574702565,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 67263677HCID 67263677, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.519 g, 2.36 mmol), Pyridine (0.420 mL, 5.19 mmol), 4-Dimethylaminopyridine (21 mg, 0.17 mmol) and anhydrous 1,2-Dichloroethane (8.5 mL) were combined in a round bottom flask. α-Phthalimidoacetyl Chloride (1.105 g, 4.942 mmol) was added to the mixture and it was stirred at room temperature for 16.5 hours. The reaction was concentrated under reduced pressure and purified by normal phase chromatography to yield a yellow solid, 2-[2-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-2-oxo-ethyl]-isoindole-1,3-dione (55%) LCMS: m/z=408.11 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.21 (m, 2H), 7.87 (m, 2H), 7.74 (m, 3H), 4.74 (m, 1H), 4.55 (d, 1H, J=16.9), 4.55 (d, 1H, J=16.7), 2.68 (m, 1H), 2.23 (m, 1H), 1.83 (m, 1H), 1.68 (m, 1H), 1.51 (m, 6H), 1.26 (m, 1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-5d5c7ebd212444e0aa5a17c84bd44d34
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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