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

HRID 597062Notes

Reaction equation

HRID 597062 reaction equation
N[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][CH3:27])=[O:25])=[C:13]3[CH3:28])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[ClH:38]>C(O)(=O)C.O>[Cl:38][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][CH3:27])=[O:25])=[C:13]3[CH3:28])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 517045Sodium AcetateHCID 21449377HCID 21449377, compoundHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of methyl 1-(7-aminoquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate (0.5g.) in acetic acid (12 ml.) was treated with concentrated hydrochloric acid (1.5 ml.). The solution obtained was stirred at 0°-5° C during the addition, over 15 minutes, of a solution of sodium nitrite (0.15g.) in water (2 ml.). The dark red solution was added dropwise to a solution of cuprous chloride (0.2g.) in concentrated hydrochloric acid (5ml.) kept at room temperature. The mixture was then stirred for 1 hr. before addition of sufficient sodium acetate to adjust the pH of the mixture to 4-5. The mixture was then concentrated in vacuo and the residue treated with water (100ml.) and ethyl acetate (50ml.). The aqueous layer was extracted with ethyl acetate (2 × 30ml.) and the extracts washed with saturated sodium hydrogen carbonate solution (2 × 30ml.). After being washed with water (30ml.) and dried(Na2SO4), evaporation of the extracts in vacuo gave an oil, which slowly solidified to give methyl 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methyl-indol-3-ylacetate as a yellow solid, m.p. 111°-114° C.

Workup

  1. customThe solution obtained
  2. customkept at room temperature
  3. concentrationThe mixture was then concentrated in vacuo
  4. additionthe residue treated with water (100ml.) and ethyl acetate (50ml.)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2 × 30ml.)
  6. washthe extracts washed with saturated sodium hydrogen carbonate solution (2 × 30ml.)
  7. washAfter being washed with water (30ml.) and dried(Na2SO4), evaporation of the extracts in vacuo
  8. customgave an oil, which

Sources & evidence

ORD record
ord-c10100f1f49d4d9aaeb157fdfd6ddbb5
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

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