Triethylamine → 8-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide

HRID 1243133Notes

Reaction equation

HRID 1243133 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]2.S(O)(O)(=O)=O.[CH2:20]([N:22]([CH2:30][CH3:31])[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[CH3:21].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:30]([N:22]([CH2:20][CH3:21])[C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:12]([CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=3)[CH2:10]2)=[O:14])=[CH:25][CH:24]=1)[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 80166N,N-Diethyl-p-phenylenediamine sulfateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 219404338-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 443913428-Hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amideYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This phenol from Example 6A was dissolved in DMF (4.0 mL) and N,N-Diethyl-benzene-1,4-diamine sulfate (602 mg, 2.3 mmol), Et3N (707 mg, 7.0 mmol), and TBTU (738 mg, 2.3 mmol) were added at ambient temperature. The mixture was stirred overnight and purified by silica gel column chromatography to provide 8-hydroxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide (480 mg, 62%).

Workup

  1. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4a07c33681b43c49a2f29681394d0f9
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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