Water → Ethyl 2-(8-chloro-6-cyano-2,3-dihydro-5-oxopyrrolo[1,2,3-de]-1,4-benzoxazine-6-yl)-2-cyanoacetate

HRID 34979Notes

Reaction equation

HRID 34979 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[O:9][CH2:8][CH2:7][N:6]3[C:10](=[O:26])[C:11]([CH:18]([C:24]#[N:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH2:14][N+:15]([O-])=O)[C:12]([CH:13]=1)=[C:5]23.P(Cl)(Cl)Cl.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[O:9][CH2:8][CH2:7][N:6]3[C:10](=[O:26])[C:11]([CH:18]([C:24]#[N:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])([C:14]#[N:15])[C:12]([CH:13]=1)=[C:5]23

Participants

5

Reactant 3

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 21297532HCID 21297532, compound

Product 1

HCID 14152290Ethyl 2-(8-chloro-6-cyano-2,3-dihydro-5-oxopyrrolo[1,2,3-de]-1,4-benzoxazine-6-yl)-2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-(8-chloro-2,3-dihydro-6-nitromethyl-5-oxopyrrolo[1,2,3-de]-1,4-benzoxazine-6-yl)-2-cyanoacetate (3 g) in pyridine (30 ml) was added phosphorous trichloride (1.6 g) on an ice bath, and stirred at room temperature for 4.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After removal of solvent, the title compound was obtained as dark reddish oil (0.9 g, 33%) by purification.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter removal of solvent

Sources & evidence

ORD record
ord-71d01328791b4c6aa6f0ba4c99b01a8a
Source dataset
uspto-grants-1988_08
Patent number
US04764608

Reaction notes

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