Hydrogen Bromide → Ethyl 1-(7-chloroquinazolin-4-yl)-5-hydroxy-2-methylindol-3-ylacetate

HRID 597060Notes

Reaction equation

HRID 597060 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[C:27]3[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=1)[C:13]([CH3:29])=[C:12]2[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])C1C=CC=CC=1.Br.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[Cl:28][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([N:14]3[C:15]4[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=4)[C:12]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:13]3[CH3:29])=[N:19][CH:20]=[N:21]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 517045Sodium AcetateHCID 21449403Ethyl 5-benzyloxy-1-(7-chloroquinazolin-4-yl)-2-methylindol-3-ylacetate

Product 1

HCID 21449352Ethyl 1-(7-chloroquinazolin-4-yl)-5-hydroxy-2-methylindol-3-ylacetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of ethyl 5-benzyloxy-1-(7-chloroquinazolin-4-yl)-2-methylindol-3-ylacetate (1.5g) in glacial acetic acid (5ml.) was treated with a 50% w/v solution of hydrogen bromide in glacial acetic acid (5ml.). The resulting dark red solution was stirred at room temperature for 10 minutes and then neutralised by the addition to a mixture of saturated sodium acetate solution (50ml.) and water (150ml.). The mixture was extracted with ethyl acetate (3 × 50ml.) and the extracts washed successively with water (2 × 40ml.), saturated sodium hydrogen carbonate solution (2 × 40ml.), water (40ml.) and then saturated sodium chloride solution (40ml.). After drying (MgSO4), the extracts gave on evaporation in vacuo a yellow-brown oil. Purification by chromatography on silica gel (200g.) in a mixture of 50% v/v ether and 50% v/v petroleum ether (b.p 40°-60° C.), gave ethyl 1-(7-chloroquinazolin-4-yl)-5-hydroxy-2-methylindol-3-ylacetate as a pale yellow glass [NMR: 2-CH3 at 7.7 τ; pure by TLC (systems A, C and D)].

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3 × 50ml.)
  2. washthe extracts washed successively with water (2 × 40ml.), saturated sodium hydrogen carbonate solution (2 × 40ml.), water (40ml.)
  3. dry with materialAfter drying (MgSO4)
  4. customthe extracts gave on evaporation in vacuo a yellow-brown oil
  5. customPurification by chromatography on silica gel (200g.)
  6. additionin a mixture of 50% v/v ether and 50% v/v petroleum ether (b.p 40°-60° C.)

Sources & evidence

ORD record
ord-6b9b6bdc3d0c401fb18fa0c409f3516a
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

Loading…