Quinone → Methyl 1(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate

HRID 597048Notes

Reaction equation

HRID 597048 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]3[C:21]4[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=4)[CH:15]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:14]3[CH3:29])=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(=O)C=CC(=O)C=C1.C([O-])(=O)C.[Na+]>CN(C)C=O.O>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]3[C:21]4[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=4)[C:15]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:14]3[CH3:29])=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 4650QuinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 517045Sodium AcetateHCID 86734552HCID 86734552, compound

Product 1

HCID 21449337Methyl 1(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindolin-3-ylacetate hydrochloride (2.15g.) in dry dimethylformamide (50ml.; dried with calcium hydride) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.2g.). The mixture was heated on a steam bath for 2 hours and then an additional portion of the benzoquinone derivative (0.6g.) was added. After further heating for 1 hour, the solution was poured into water (500ml.) containing anhydrous sodium acetate (10g.). The mixture was extracted with chloroform (3 × 100ml.) and the solid residue, at the solvent interface, discarded. The chloroform extracts were washed successively with water, saturated sodium bicarbonate solution, water and brine, and then dried (MgSO4). Evaporation of the solution gave an oil, which was purified by chromatography on silica gel (100g.) in an increasing gradient of ether in petroleum ether (b.p. 40°-60° C.) (polarity increased by incremental addition of 10% v/v ether) to give methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate as a yellow solid, m.p. 112°-114° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for 2 hours
  2. temperatureAfter further heating for 1 hour
  3. extractionThe mixture was extracted with chloroform (3 × 100ml.)
  4. washThe chloroform extracts were washed successively with water, saturated sodium bicarbonate solution, water and brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solution
  7. customgave an oil, which
  8. customwas purified by chromatography on silica gel (100g.) in an increasing gradient of ether in petroleum ether (b.p. 40°-60° C.) (polarity
  9. temperatureincreased by incremental addition of 10% v/v ether)

Sources & evidence

ORD record
ord-af2dbd180d7c409e8429de18bdc5e802
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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