Arsenic Acid → 8-Methylquinoline-7-carboxylic acid

HRID 1174668Notes

Reaction equation

HRID 1174668 reaction equation
[NH2:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[As](=O)(O)(O)O.O[CH2:18][CH:19]([CH2:21]O)O.S(=O)(=O)(O)O>O.C(Cl)(Cl)Cl>[CH3:11][C:3]1[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[C:10]2[C:2]=1[N:1]=[CH:21][CH:19]=[CH:18]2

Participants

7

Reactant 4

HCID 234Arsenic AcidHCID 753GlycerolHCID 1118Sulfuric AcidHCID 27336993-Amino-2-methylbenzoic acid

Product 1

HCID 597495658-Methylquinoline-7-carboxylic acidYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 3-amino-2-methylbenzoic acid (Intermediate M1) (6.06 g, 39.6 mmol) (commercially available from Aldrich) and arsenic acid (H5AS3O10) 7.43 g (commercially available from VWR/ALFA) in glycerol (5.8 mL, 79.2 mmol), and sulfuric acid (9 mL) was heated to 160° C. for 5 h. The mixture was cooled to rt, diluted with water and filtered through a bed of diatomaceous earth. The pH was adjusted to pH 6-7 with 2 M NaOH. The aqueous layer was exhaustively extracted with CHCl3:MeOH (3:1). The organic fractions were pooled and evaporated under vacuum to give a solid. This solid was titurated with CHCl3, and collected on a glass frit. The solid material was washed with hexanes and dried under high vacuum to give a pure solid, 8-methylquinoline-7-carboxylic acid (intermediate M2) 3.86 g (51%).

Workup

  1. filtrationfiltered through a bed of diatomaceous earth
  2. extractionThe aqueous layer was exhaustively extracted with CHCl3:MeOH (3:1)
  3. customevaporated under vacuum
  4. customto give a solid
  5. customcollected on a glass frit
  6. washThe solid material was washed with hexanes
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-67ae4dab32074996aef7e2476e30eb8d
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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