Glycolic Acid → HCID 68089188, compound

HRID 1772002Notes

Reaction equation

HRID 1772002 reaction equation
[CH3:1][NH:2][C:3]1[C:12]([NH2:13])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[OH:14][CH2:15][C:16](O)=O.C(=O)(O)[O-].[Na+]>>[CH3:1][N:2]1[C:3]2[CH:4]=[CH:5][C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[C:12]=2[N:13]=[C:16]1[CH2:15][OH:14]

Participants

4

Reactant 3

HCID 757Glycolic AcidHCID 516892Sodium BicarbonateHCID 29971707N~7~-Methylquinoline-7,8-diamine

Product 1

HCID 68089188HCID 68089188, compoundYield 83%

Conditions

Temperature
115 °C

Procedure

A mixture of N7-methylquinoline-7,8-diamine (1.0 g, 5.8 mmol) and 2-hydroxy acetic acid (2.2 g, 29 mmol) was stirred at 115° C. for 2 h. Then saturated sodium bicarbonate solution was added. The mixture was extracted with EtOAc. The organic layer was concentrated to give a residue which was purified by silica gel column chromatography (eluting with DCM/MeOH v/v 30:1) to give (3-methyl-3H-imidazo-[4,5-h]quinolin-2-yl)methanol as a yellow solid (1.0 g, yield 83%). ESI MS: m/z 214 [M+H]+.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customto give a residue which
  4. customwas purified by silica gel column chromatography (
  5. washeluting with DCM/MeOH v/v 30:1)

Sources & evidence

ORD record
ord-84488c68e7024af4a5371145d0e16202
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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