3-Methoxyaniline → HCID 14650683, compound

HRID 982266Notes

Reaction equation

HRID 982266 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[N+](C1C=CC([O:17][C:18]([O:20][CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:25][C:24]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:23][CH2:22]2)=O)=CC=1)([O-])=O>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:18]([O:20][CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:25][C:24]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[N:23][CH2:22]2)=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 108243-MethoxyanilineHCID 14650635HCID 14650635, compound

Product 1

HCID 14650683HCID 14650683, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

meta-Anisidine (1.72 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-5-(4-nitrophenoxycarbonyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (3 g) and 4-(dimethylamino)pyridine (0.3 g) in anhydrous N,N-dimethylformamide (50 cc). The solution obtained is heated to a temperature in the region of 70° C. for 6 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by chromatography on silica (0.063-0.2 mm; 50 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate/triethylamine (65:30:5 by volume)], collecting 25-cc fractions. Fractions 2 to 5 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-5-(3-methoxyphenylcarbamoyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (1.8 g), m.p. 110° C. is obtained.

Workup

  1. customThe solution obtained
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  3. customThe residue is purified by chromatography on silica (0.063-0.2 mm; 50 g)
  4. customcollecting 25-cc fractions
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  6. customAfter recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-bc601e5bb3d14661b86f9ce35bf69833
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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