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

HRID 224934Notes

Reaction equation

HRID 224934 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 (4.5 g., 0.013 moles) in ethanol (9.5 ml) and the solution left to stand at room temperature for 48 hours. Removal of solvent gave the title compound as an orange oil (3.2 g., 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--), 4.31(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-ada1904c74b843f798e15f8255c8d9f9
Source dataset
uspto-grants-1980_11
Patent number
US04234726

Reaction notes

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