1,2-Dibromoethane → 7-Nitro-3,4-dihydro-2H-1,4-benzoxazine

HRID 1030968Notes

Reaction equation

HRID 1030968 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[H-].[Na+].Br[CH2:15][CH2:16]Br>CN(C)C=O>[N+:9]([C:7]1[CH:6]=[CH:5][C:3]2[NH:4][CH2:15][CH2:16][O:1][C:2]=2[CH:8]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following Intermediate Method 4, the reaction of 2-hydroxy-4-nitroaniline with sodium hydride and 1,2-dibromoethane in N,N-dimethylformamide produces 2,3-dihydro-7-nitro-1,4-benzoxazine, (XIX). The reaction of (XIX) with sodium hydride and 2-iodopropane in N,N-dimethylformamide yields 2,3-dihydro-4-(1-methylethyl)-7-nitro-1,4-benzoxazine, (XX). Hydrogenation of (XX) with platinum oxide yielded (XXI). ##STR31##

Sources & evidence

ORD record
ord-3bdb541ff4f24aec9ff7a741a522a333
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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