Sulfuric Acid → 3-(Methoxymethyl)-8-quinolinol

HRID 1198723Notes

Reaction equation

HRID 1198723 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[N+](C1C=CC=CC=1O)([O-])=O.[CH3:24][O:25][C:26]([C:28](=[CH2:30])[CH3:29])=O.[OH-].[Na+]>O.CO>[CH3:24][O:25][CH2:26][C:28]1[CH:29]=[N:6][C:7]2[C:12]([CH:30]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 58012-AminophenolHCID 6658Methyl MethacrylateHCID 69472-NitrophenolHCID 14798Sodium Hydroxide

Product 1

HCID 110087013-(Methoxymethyl)-8-quinolinol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methanol and sulfuric acid (10.0 g, 0.1 mol) is heated to 65° C., treated with o-aminophenol (4.36 g, 0.04 mol) and o-nitrophenol (2.78 g, 0.02 mol), heated to 70° C., treated with methoxymethacrolein (6.0 g, 0.06 mol) over 40 minutes at 85° to 90° C. and diluted with water. The aqueous mixture is adjusted to about pH 2 with 50% sodium hydroxide solution and filtered. The filtrate is adjusted to about pH 7 with 50% sodium hydroxide solution and extracted with chloroform. The combined organic extracts are concentrated in vacuo to give the title product as a solid which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. filtrationfiltered
  2. extractionextracted with chloroform
  3. concentrationThe combined organic extracts are concentrated in vacuo

Sources & evidence

ORD record
ord-f512d3e50fe24885b5e3fbb2e58e9b0c
Source dataset
uspto-grants-1994_01
Patent number
US05281713

Reaction notes

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