Methylamine → 4-(1-Naphthyl)-2,2-dimethyl-7-(3-methylamino-2-hydroxy-propoxy)-2H chromene

HRID 2163365Notes

Reaction equation

HRID 2163365 reaction equation
[CH3:1][NH2:2].[O:3]1[CH2:29][CH:4]1[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)=[CH:12][C:13]([CH3:18])([CH3:17])[O:14]2)=[CH:9][CH:8]=1>C(O)C>[C:19]1([C:11]2[C:10]3[C:15](=[CH:16][C:7]([O:6][CH2:5][CH:4]([OH:3])[CH2:29][NH:2][CH3:1])=[CH:8][CH:9]=3)[O:14][C:13]([CH3:18])([CH3:17])[CH:12]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 233307422,2-Dimethyl-4-(naphthalen-1-yl)-7-[(oxiran-2-yl)methoxy]-2H-1-benzopyran

Product 1

HCID 544257434-(1-Naphthyl)-2,2-dimethyl-7-(3-methylamino-2-hydroxy-propoxy)-2H chromeneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylamine (9.5 ml) was added to 7-(2,3-epoxypropoxy)-2,2-dimethyl-4-(1-naphthyl)-2H chromene (4.5g., 0.013 moles) in ethanol (9.5ml) and the solution left to stand at room temperature for 48 hours. Removal of solvent gave the title compound as an orange oil (3.2g., 63%). N.M.R. (τCDCl3) 8.54(s, 3H, CH3 -), 8.48(s, 3H, CH3 -), 7.06(s, 3H, N-CH3), 6.72(d, 2H, -CHCH2 -), 6.05(d, 2H, -CH2CH-), 4.51(s, 1H, vinylic CH), 3.40-3.80 (m, 3H, aromatic H'5), 2.10-2.75(m, 7H, aromatic H's).

Workup

  1. waitthe solution left
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-876a02b3e0024f9dbf12552e6fc1d505
Source dataset
uspto-grants-1979_01
Patent number
US04133883

Reaction notes

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