HCID 2794448, compound → HCID 21257365, compound

HRID 636073Notes

Reaction equation

HRID 636073 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([O:13]C)[CH:10]=[C:9]2[C:4]=1[C:5]([CH3:16])=[CH:6][C:7](=[O:15])[NH:8]2.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(Cl)Cl.CO>ClC1C=CC=CC=1>[OH:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]2[C:4]=1[C:5]([CH3:16])=[CH:6][C:7](=[O:15])[NH:8]2

Participants

5

Reactant 3

HCID 2794448HCID 2794448, compoundHCID 6451240Aluminum(III) ChlorideHCID 21584188Chloroform methanol

Product 1

HCID 21257365HCID 21257365, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a stirred solution of compound 11 (12.5 g, 57.07 mmol) in chlorobenzene (100 mL), aluminium chloride (37 g, 285.3 mmol) was added in portions over a period of 10 min and heated at 100° C. overnight (TLC chloroform: methanol 9:1, Rf=0.2). The reaction mixture was then cooled to room temperature, poured on crushed ice (300 g) and stirred well for 30 min. The solid separated was filtered washed with water till neutral to pH. It was then washed with hexane (50 mL) and dried to give product 5,7-dihydroxy-4-methyl-1,2-dihydro-2-quinolinone (13, 10.5 g) in 96% yield as a dark brown solid. M.P. >300° C.

Workup

  1. additionpoured
  2. customThe solid separated
  3. filtrationwas filtered
  4. washwashed with water till neutral
  5. washIt was then washed with hexane (50 mL)
  6. customdried

Sources & evidence

ORD record
ord-86af25b5c5fc447892498fb032a94565
Source dataset
uspto-grants-2001_02
Patent number
US06191279B1

Reaction notes

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