3-(Dimethylamino)phenol → 3-Dimethylaminophenyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerate

HRID 393874Notes

Reaction equation

HRID 393874 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:4][C:3]1=[O:20].[CH3:21][N:22]([CH3:30])[C:23]1[CH:24]=[C:25](O)[CH:26]=[CH:27][CH:28]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C1COCC1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([N:22]([CH3:30])[CH3:21])[CH:28]=2)=[O:18])=[CH:4][C:3]1=[O:20]

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 10868DicyclohexylcarbodiimideHCID 226478225-[(1,2-Dioxo-1,2-dihydronaphth-4-yl)oxy]valeric Acid

Product 1

HCID 98007193-Dimethylaminophenyl 5-[(1,2-dihydro-1,2-dioxonaphth-4-yl)oxy]valerateYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of acid 3 (137 mg, 0.5 mmol), 3-dimethylaminophenol (82 mg, 0.6 mmol), DCC (103 mg, 0.5 mmol), and DMAP (12 mg, 0.01 mmol) in THF (2 mL) was stirred for 2 h. The reaction mixture was concentrated in vacuo, the residue dissolved in benzene, washed with H2O and dried (Na2SO4). Column chromatography (10% EtOAc) in benzene gave 13 as a yellow solid (70 mg, 36%), 1H NMR (CDCl3) 8.13, (d, J=7.3 Hz, 1H), 7.90 (d, J=7.4 Hz, 1H), 7.69 (t, J=6.1 Hz, 1H), 7.58 (t, J=7.6 Hz, 1H), 7.22 (dd, J=8.1, 8.1 Hz, 1H), 6.30-6.70 (m, 2H), 5.96 (s, 1H), 4.21 (t, J=5.6 Hz, 2H), 2.69 (t, J=6.5 Hz, 2H), 1.90-2.15 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in benzene
  3. washwashed with H2O
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-cd1d138584874f81ac76ac8bb285d186
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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