N-Methoxy-1-naphthalenemethanamine → 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-N-naphthalen-1-ylmethyl-acetamide

HRID 2214682Notes

Reaction equation

HRID 2214682 reaction equation
[CH3:1][O:2][NH:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:15][C:16]1([CH3:26])[O:20][C:19](=[CH:21][C:22](O)=[O:23])[C:18](=[O:25])[O:17]1>>[CH3:15][C:16]1([CH3:26])[O:20][C:19](=[CH:21][C:22]([N:3]([O:2][CH3:1])[CH2:4][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)=[O:23])[C:18](=[O:25])[O:17]1

Participants

3

Reactant 2

HCID 15611168N-Methoxy-1-naphthalenemethanamineHCID 68860642(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid

Product 1

HCID 738555772-(2,2-Dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-N-naphthalen-1-ylmethyl-acetamideYield 56%

Procedure

O-Methyl-N-naphthalen-1-ylmethyl-hydroxylamine was reacted with (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid according to the method described for the preparation of compound 90-B to give the title compound as a pale yellow solid (0.826 g, 56% yield). 1HNMR (300 MHz, CDCl3) δ: 8.18 (1H, d, J=8.05 Hz), 7.85 (2H, t, J=9.15 Hz), 7.56–7.41 (4H, m), 6.40 (1H, s), 5.30 (2H, s), 3.43 (3H, s), 1.77 (6H, s).

Sources & evidence

ORD record
ord-7dd4baf1f87f475f8442b5183309e8cc
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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