N-Methylaniline → HCID 54710169, compound

HRID 1080642Notes

Reaction equation

HRID 1080642 reaction equation
C(O[C:4]([C:6]1[C:18](=[O:19])[N:14]2[CH2:15][CH2:16][O:17][C:12]3[C:13]2=[C:8]([CH:9]=[CH:10][CH:11]=3)[C:7]=1[OH:20])=[O:5])C.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[OH:20][C:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:13]=2[N:14]([CH2:15][CH2:16][O:17]3)[C:18](=[O:19])[C:6]=1[C:4](=[O:5])[N:22]([CH3:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 54710203HCID 54710203, compound

Product 1

HCID 54710169HCID 54710169, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2,3-dihydro-6-ethoxycarbonyl-7-hydroxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (6 g) and N-methylaniline (4 ml) in pyridine (30 ml) was stirred at 125° C. for 4 hours. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (200 g) eluting with a mixture of chloroform and methanol (5:1). The product was recrystallized from a mixture of ethanol and isopropyl ether to give pale brown crystals of 2,3-dihydro-7-hydroxy-6-(N-methyl-N-phenylcarbamoyl)-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.7 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica gel (200 g)
  3. washeluting with a mixture of chloroform and methanol (5:1)
  4. customThe product was recrystallized from a mixture of ethanol and isopropyl ether

Sources & evidence

ORD record
ord-1347d8f94e9f4b19a525bb93aad0d3a8
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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