N,N-Diethyl-p-phenylenediamine → N-(4-(Diethylamino)phenyl)-8-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1243131Notes

Reaction equation

HRID 1243131 reaction equation
CO[C:3]([C:5]1([CH3:17])[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[CH2:18]([N:20]([CH2:28][CH3:29])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH3:19].CC[Mg+].[Br-]>C1COCC1>[CH2:28]([N:20]([CH2:18][CH3:19])[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:3]([C:5]2([CH3:17])[CH2:14][CH2:13][C:12]3[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:4])=[CH:23][CH:22]=1)[CH3:29]

Participants

5

Reactant 3

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 695851218-Methoxy-2-methyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl esterHCID 178461630HCID 178461630, compound

Product 1

HCID 11187726N-(4-(Diethylamino)phenyl)-8-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxamideYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The ester from Example 2A (170 mg, 0.73 mmol) was dissolved in THF (2.0 mL) and a solution (3.0 mL) of N,N-Diethyl-benzene-1,4-diamine (332 mg, 2 mmol) and EtMgBr (2.0 mmol) in THF was added at 0° C. The reaction mixture was quenched with aqueous NH4Cl after 3 hours. The mixture was extracted with ethyl acetate (3×15 mL) and the combined extracts were dried over MgSO4 and purified by column chromatography to provide the titled compound (30 mg, 8%). 1H NMR (400 MHz, DMSO-D6) δ 9.03 (s, 1H), 7.33 (d, J=9.2 Hz, 2H), 7.03 (t, J=8.0 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.73 (d, J=8.0 Hz, 1H), 6.58 (d, J=9.2 Hz, 2H), 3.77 (s, 3H), 3.27 (q, J=7.2 Hz, 4H), 3.11 (d, J=17.2 Hz, 1H), 2.74 (t, J=6.4 Hz, 2H), 2.43 (d, J=17.2 Hz, 2H), 2.15 (ddd, J=6.4, 6.4, 13.2 Hz, 1H), 1.73 (ddd, J=7.2, 7.2, 13.6 Hz, 1H), 1.26 (s, 3H), and 1.04 (t, J=7.2 Hz, 6H). MS (ESI) positive ion 367 (M+H)+; negative ion 365 (M−H)−.

Workup

  1. customThe reaction mixture was quenched with aqueous NH4Cl after 3 hours
  2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-958359a20fae431d93babc0c2ef23eac
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

Loading…