Methanol → HCID 21449337, compound

HRID 597067Notes

Reaction equation

HRID 597067 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([OH:26])=[O:25])=[C:13]3[CH3:27])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.CO.[C:34]([O-])(=O)C.[Na+]>C(O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([O:26][CH3:34])=[O:25])=[C:13]3[CH3:27])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 517045Sodium AcetateHCID 101940031-(7-Chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid

Product 1

HCID 21449337HCID 21449337, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of anhydrous 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid (1.0g.) in ethanol-free chloroform (30 ml; dried over calcium chloride) was added a solution of thionyl chloride (0.19 ml.) in chloroform (2ml). The resulting dark red solution was stirred at room temperature for 30 mins., and then methanol (20 ml.) was added. The mixture was heated under reflux for 30 mins., saturated sodium acetate solution (2 ml.) was added, and the mixture was concentrated in vacuo. Water (30 ml.) was added to the residue and the mixture was extracted with ether (3 × 30 ml.). The ether extracts were washed successively with saturated sodium hydrogen carbonate solution (30 ml.) and water (30 ml.), and dried (Na2SO4). Evaporation of the solvent gave a dark yellow oil, which slowly crystallised to give methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate, m.p. 112°-114° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 mins
  3. concentrationthe mixture was concentrated in vacuo
  4. additionWater (30 ml.) was added to the residue
  5. extractionthe mixture was extracted with ether (3 × 30 ml.)
  6. washThe ether extracts were washed successively with saturated sodium hydrogen carbonate solution (30 ml.) and water (30 ml.)
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. customgave a dark yellow oil, which
  10. customslowly crystallised

Sources & evidence

ORD record
ord-9fa89b6832194ee3a953211cb7b9b4c4
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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