Diethyl Ether → HCID 13424113, compound

HRID 483689Notes

Reaction equation

HRID 483689 reaction equation
[Li]C.CCOCC.O([NH2:10])C.[Li][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH2:20][CH:19]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]2>CCCCCC>[NH2:10][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[CH2:20][CH:19]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4113O-MethylhydroxylamineHCID 178418348HCID 178418348, compoundHCID 178506661HCID 178506661, compound

Product 1

HCID 13424113HCID 13424113, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-15 °C

Procedure

A stirred solution (9.2 ml) of 0.92M MeLi in ether (8.5 mmol) of methoxylamine in hexane (9 ml) was added dropwise (1 drop/s) followed by 2.6 ml (4.3 mmol) of a 1.55M solution of 5, 6, 7 or 8-lithio-2-(di-n-propylamino)tetralin (prepared from 5, 6, 7 or 8-bromo-2-(di-n-propylamino)tetralin and n-BuLi). The mixture was warmed to -15° C. for 2 hr and quenched with water (0.5 ml). Workup of the resulting mixture afforded the desired 5, 6, 7 or 8-amino-2-(dinpropylamino)tetralin.

Workup

  1. customquenched with water (0.5 ml)
  2. customWorkup of the resulting mixture afforded the

Sources & evidence

ORD record
ord-148e056b290a4fb8a0f554be7f47c730
Source dataset
uspto-grants-1993_07
Patent number
US05225596

Reaction notes

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