Allyl bromide → 8-(Allyloxy)-N-(4-(diethylamino)phenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1243134Notes

Reaction equation

HRID 1243134 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([OH:23])[CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:32](Br)[CH:33]=[CH2:34]>CN(C=O)C>[CH2:34]([O:23][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH2:14][CH:13]([C:11]([NH:10][C:7]1[CH:6]=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:24][CH3:25])=[CH:9][CH:8]=1)=[O:12])[CH2:22][CH2:21]2)[CH:33]=[CH2:32]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 443913428-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide

Product 1

HCID 112803968-(Allyloxy)-N-(4-(diethylamino)phenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The phenol from Example 6B (68 mg, 0.2 mmol) was dissolved in DMF (0.4 mL) and K2CO3 (41 mg, 0.2 mmol) and allyl bromide (36 mg, 0.3 mmol) were added at ambient temperature. The reaction mixture was worked up and purified by column chromatography to provide the titled compound (15 mg, 20%). 1H NMR (400 MHz, DMSO-D6) δ 9.59 (s, 1H), 7.39 (d, J=9.2 Hz, 2H), 7.05 (t, J=8.0 Hz, 1H), 6.75 (d, J=8.0 Hz, 1H), 6.70 (d, J=8.0 Hz, 1H), 6.61 (d, J=9.2 Hz, 2H), 6.05 (ddddd, 5.2, 5.2, 10.8, 16.0 Hz, 1H), 5.39 (dddd, J=1.2, 1.2, 1.2, 15.2 Hz, 1H), 5.24 (dddd, J=1.2, 1.2, 1.2, 10.4 Hz, 1H), 4.55 (m, 2H), 3.28 (q, J=6.8 Hz, 4H), 2.3 (m, 1H), 2.79 (m, 2H), 2.61 (m, 2H), 1.99 (m, 1H), 1.69 (m, 1H), and 1.06 (t, J=6.8 Hz, 6H). MS (ESI) positive ion 379 (M+H)+; negative ion 377 (M−H)−.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-2ab0b44a4a7f401e93bd1eee47d7755c
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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