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

HRID 838910

Reaction equation

HRID 838910 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's), 2.10-2.75(m, 7H, aromatic H's).

Workup

  1. waitthe solution left
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-85338c0b14c445b9b7ea6e29d9ce55bd
Source dataset
uspto-grants-1978_06
Patent number
US04093631

Linked notes

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