Ethanol → HCID 69978275, compound

HRID 2302014Notes

Reaction equation

HRID 2302014 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[CH:13]=2)[NH:8][C:7]1=[O:17])[CH3:2].[O-]CC.[Na+].C(O)C.[C:26]([O:30][C:31](=[O:37])[NH:32][CH2:33][CH2:34][CH2:35]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O.C(Cl)(Cl)Cl.CO.O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH2:35][CH2:34][CH2:33][NH:32][C:31]([O:30][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:37])[CH:13]=2)[NH:8][C:7]1=[O:17])[CH3:2]

Participants

9

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 12071334HCID 12071334, compound

Product 1

HCID 69978275HCID 69978275, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (6-hydroxy-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-acetic acid ethyl ester (2.0 g, 8.0 mmol) in N,N-dimethylformamide (16 mL) was treated with a solution of sodium ethoxide (21 wt %) in ethanol (3.0 mL, 8.0 mmol) at rt and after 15 min, (3-bromopropyl)-carbamic acid tert-butyl ester (1.9 g, 8.0 mmol) was added. After 4 days, the solution was treated with water (75 mL) and the resulting gum was briefly heated, then cooled to 0° C. The precipitated solid was triturated for 6 h, to give the crude product (2.7 g). Flash chromatography (90 g silica; CHCl3, then 1% MeOH (saturated with NH3) —CHCl3) gave the title compound (2.6 g, 79% yield) as a white solid.

Workup

  1. temperaturethe resulting gum was briefly heated
  2. customThe precipitated solid was triturated for 6 h
  3. customto give the crude product (2.7 g)

Sources & evidence

ORD record
ord-946cf3a99c2c4c6d9141f6fb9c3bc2f5
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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