4-Aminophenol → 4-[2-(Dimethylamino)ethoxy]aniline

HRID 964634Notes

Reaction equation

HRID 964634 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]O>C1COCC1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 79022-(Dimethylamino)ethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 64846554-[2-(Dimethylamino)ethoxy]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 4-[2-(dimethylamino)ethoxy]aniline to generate the title compound. The 4-[2-(dimethylamino)ethoxy]aniline was prepared by treating commercial 4-aminophenol with DEAD, φ3P, and 2-(dimethylamino)ethanol in THF.

Sources & evidence

ORD record
ord-9567b5c0e3414b29be3b082fe5caf6b6
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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