Acetic Anhydride → 2-[1-(7-Chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]ethyl acetate

HRID 597058Notes

Reaction equation

HRID 597058 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][CH2:24][OH:25])=[C:13]3[CH3:26])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C1C=CC=CC=1>[C:27]([O:25][CH2:24][CH2:23][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[C:13]=1[CH3:26])(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21449343HCID 21449343, compound

Product 1

HCID 214493952-[1-(7-Chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]ethyl acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-(7-chloroquinazolin-4-yl)-3-(2-hydroxyethyl)-5-methoxy-2-methylindole (0.6g.) and acetic anhydride (0.4g.) in benzene (20ml.; dried over sodium wire) was refluxed for 15 hours. The resulting yellow solution was cooled and washed successively with saturated sodium hydrogen carbonate solution (2 × 20ml.) and water (20ml.), and dried (MgSO4). The solution was evaporated to give 2-[1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]ethyl acetate as an oil [pure by TLC (system A) and having a satisfactory NMR spectrum (--OCH3 τ 6.18)].

Workup

  1. temperatureThe resulting yellow solution was cooled
  2. washwashed successively with saturated sodium hydrogen carbonate solution (2 × 20ml.) and water (20ml.)
  3. dry with materialdried (MgSO4)
  4. customThe solution was evaporated

Sources & evidence

ORD record
ord-8e326de9692c421f88e24d598543d697
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

Loading…