Morpholine → Methanol

HRID 1454010Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Br:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=[O:26])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20].N1CC[O:30][CH2:29]C1>>[Br:12][C:13]1[CH:14]=[C:15]([CH:23]2[C:8]3[C:7](=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=3)[O:11][CH:25]([OH:26])[CH2:24]2)[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20].[CH3:29][OH:30]

Participants

Reactant 3

HCID 8083Morpholine

HCID 121243-Hydroxyacetanilide

HCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 2

HCID 887MethanolYield 26%

HCID 9979619N-[4-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-chroman-7-yl]-acetamide

Procedure

The title compound was prepared following the procedure as in Example 18 from 3-acetamido phenol (13 mg; 0.086 mmol) and 3-(3-bromo-4,5-dimethoxy-phenyl)-propenal (25 mg; 0.09 mmol) using morpholine (15 μl; 0.17 mmol) as a base in reluxing methanol (1 ml) (7 h) (yield: 26%). 1H NMR (acetone-d6): 9.06 (s, 1H), 7.36 and 7.34 (broad s each, 1H), 6.89-7.01 (m, 3H), 6.57-6.62 (overlapping d, J=8.4 Hz; 1H), 6.14 (d, J=6.6 Hz) and 6.11 (d, J=4.1 Hz) (1H), 5.62 (broad s) and 5.48-5.50 (m) (1H), 4.19-4.26 (overlapping dd, J=6.2, 11.1 Hz; 1H), 3.85, 3.83 and 3.79 (s each, 6H); 2.34 (broad dd, J=5.9, 12.9 Hz) and 2.09-2.18 (m) (2H), 2.04 (s overlapping with acetone-signal).

Sources & evidence

ORD record: ord-d50a1743bae8493d8cf305f3c50e49cc
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476741B2

Reaction notes

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