N-Methylisopropylamine → 3-(Isopropyl-methyl-amino)-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

HRID 991773Notes

Reaction equation

HRID 991773 reaction equation
C(O[C:5]1[C:6](=[O:18])[C:7](=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(C)C.[CH3:19][NH:20][CH:21]([CH3:23])[CH3:22]>C(#N)C>[CH:21]([N:20]([CH3:19])[C:5]1[C:6](=[O:18])[C:7](=[O:17])[C:8]=1[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 78485N-MethylisopropylamineHCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 98816173-(Isopropyl-methyl-amino)-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dioneYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a manner similar to Example 1, Step 2; 3-isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione (0.150 g, 0.609 mmol) and methyl-isopropylamine (0.07 mL, 0.670 mmol) in acetonitrile (3 mL) were converted to the title compound (0.10 g, 63%) m.p.: 109-115° C.; 1H NMR (DMSO-d6) δ7.60(m,2H), 7.07(m,2H), 4.91(m,1H), 3.81(s,3H), 1.23(br d, 6H); MS (m/z) 259 [M+].

Sources & evidence

ORD record
ord-33a14fca31b145ee9810120b056e6172
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Reaction notes

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