5-Hydroxy-2-pentanone → HCID 21449343, compound

HRID 597057

Reaction equation

HRID 597057 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)N=CC)=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[OH:25][CH2:26][CH2:27][CH2:28][C:29](=O)[CH3:30]>C(O)C>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([N:13]3[C:17]4[C:22](=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[C:28]([CH2:27][CH2:26][OH:25])=[C:29]3[CH3:30])=[N:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 140665-Hydroxy-2-pentanoneHCID 86734555HCID 86734555, compound

Product 1

HCID 21449343HCID 21449343, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acetaldehyde N1 -(7-chloroquinazolin-4-yl)p-methoxyphenylhydrazone hydrochloride (3.2g.) and 5-hydroxy-pentane-2-one (1.1g.) in ethanol (60ml.) was refluxed for 18 hours. The mixture was cooled and filtered and the filtrate evaporated in vacuo. The residue was chromatographed on silica gel (100g.) using, as eluant, petroleum ether (b.p. 40° -60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether) to give 1-(7-chloroquinazolin-4-yl)-3-(2-hydroxyethyl)-5-methoxy-2-methylindole, m.p. 148°-150° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was chromatographed on silica gel (100g.)
  5. additionpetroleum ether (b.p. 40° -60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether)

Sources & evidence

ORD record
ord-4cd57e6b87b44399bb594949dd5a8a41
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Linked notes

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