2-Butanamine, 2-methyl- → 3-(1,1-Dimethyl-propylamino)-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

HRID 991772Notes

Reaction equation

HRID 991772 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.[C:19]([NH2:24])([CH2:22][CH3:23])([CH3:21])[CH3:20]>>[CH3:20][C:19]([NH:24][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)([CH3:21])[CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 99254993-(1,1-Dimethyl-propylamino)-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dioneYield 84.1%

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 tert-amyl amine (0.48 mL, 4.11 mmol) were converted to the title compound (0.14 g, 84%) m.p.: 133-135° C.; 1H NMR (DMSO-d6) δ8.28(br s,1H), 8.04(m,2H), 7.11(m,2H), 3.83(s,3H), 1.80(q,2H), 1.42(s,6H), 0.85(t,3H); IR (KBr) 2980, 1765, 1725, 1600, 1423, 1310, 1260, 1175, 1030, 850 cm−1; MS (m/z) 273 [M+].

Sources & evidence

ORD record
ord-e9a1e8f252884a5ebd7e1b5fba5a1a15
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Reaction notes

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