Acetic Acid → HCID 20279341, compound

HRID 1633001Notes

Reaction equation

HRID 1633001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([CH:18](C#N)[C:19]([O:21]CC)=O)([C:16]#[N:17])[C:7]1=[O:26].Br.C(O)(=[O:34])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]2([CH2:18][C:19](=[O:21])[NH:17][C:16]2=[O:34])[C:7]1=[O:26]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20279346HCID 20279346, compound

Product 1

HCID 20279341HCID 20279341, compound

Procedure

A solution of ethyl 2-[1-(3,4-dichlorobenzyl)-3-cyano-5-fluoro-2-oxo-3-indolinyl]-2-cyanoacetate (E) (2.0 g.) in 48% w/v hydrogen bromide in acetic acid (25 ml.) was heated under reflux for 3 hours. The solution was evaporated to half volume and poured into water (20 ml.). The mixture was extracted with ethyl acetate (2×50 ml.). The combined extracts were washed with water (2×50 ml.), brine (50 ml.), dried (MgSO4) and evaporated. The residual solid was recrystallised from 2-propanol/petrol 60-80 to give 1'-(3,4-dichlorobenzyl)-5'-fluoro-spiro[pyrrolidine 3,3'-indoline]-2,2',5-trione (0.49 g.), m.p. 253°-254° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe solution was evaporated to half volume
  4. additionpoured into water (20 ml.)
  5. extractionThe mixture was extracted with ethyl acetate (2×50 ml.)
  6. washThe combined extracts were washed with water (2×50 ml.), brine (50 ml.)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residual solid was recrystallised from 2-propanol/petrol 60-80

Sources & evidence

ORD record
ord-50f1ada56a6949bfb7bed9017a1bb29a
Source dataset
uspto-grants-1984_10
Patent number
US04478847

Reaction notes

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