2-Amino-2-methyl-1-propanol → 4,5-Dihydro-2-[(4-methoxy-3-nitrophenyl)methyl]-4,4-dimethyloxazole

HRID 621466Notes

Reaction equation

HRID 621466 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=O)=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[O:4][CH2:3][C:2]([CH3:6])([CH3:5])[N:1]=2)=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 43305212-(4-Methoxy-3-nitrophenyl)acetic acid

Product 1

HCID 144076424,5-Dihydro-2-[(4-methoxy-3-nitrophenyl)methyl]-4,4-dimethyloxazole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 2-amino-2-methyl-1-propanol, 7.2 g (0.05 mol), (Aldrich Chemical Company) and 4-methoxy-3-nitrobenzeneacetic acid, 16.7 g (0.079 mol), (Journal of the American Chemical Society, Vol. 70, pp. 2837-2843, (1948)) is refluxed overnight in xylene, 100 ml, under a water separator. The mixture is diluted with toluene, filtered, washed with an aqueous solution of potassium bicarbonate and water. The organic layer is separated and evaporated. The resulting gum is chromatographed over silica gel and eluted with ethyl acetate to give 7.6 g of 4,5-dihydro-2-[(4-methoxy-3-nitrophenyl)methyl]-4,4-dimethyloxazole after recrystallization from hexane; mp 88°-90° C.

Workup

  1. filtrationfiltered
  2. washwashed with an aqueous solution of potassium bicarbonate and water
  3. customThe organic layer is separated
  4. customevaporated
  5. customThe resulting gum is chromatographed over silica gel
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-4ccc5e6f6fdb45ec9b03bf4b3760dc53
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Reaction notes

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