HCID 13784512, compound → HCID 15595972, compound

HRID 844921Notes

Reaction equation

HRID 844921 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH:11][CH2:12][C:13]#[CH:14])=[CH:4][C:3]=1[N:15]1[C:23](=[O:24])[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]1=[O:25]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:8][C:6]1[C:5]([NH:11][CH2:12][C:13]#[CH:14])=[CH:4][C:3]([N:15]2[C:16](=[O:25])[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=3[C:23]2=[O:24])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 1

HCID 13784512HCID 13784512, compound

Product 1

HCID 15595972HCID 15595972, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (1.22 g) was suspended in a 5% aqueous acetic acid solution, followed by heating at 80° C. A solution of 2-[2-fluoro-4-nitro-5-(2-propynyl)aminophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.75 g) in a mixture of acetic acid (2.2 ml) and ethyl acetate (2.2 ml) was dropwise added to the suspension, and the resultant mixture was heated at 70° C. for 3 hours. After removal of the precipitate by filtration, the filtrate was extracted with ethyl acetate. The extract was washed with water and an aqueous sodium bicarbonate solution, dried and concentrated to give 2-[4-amino-2-fluoro-5-(2-propynyl)aminophenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.59 g). m.p., 182.2° C.

Workup

  1. additionwas dropwise added to the suspension
  2. customAfter removal of the precipitate
  3. filtrationby filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialan aqueous sodium bicarbonate solution, dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-28653f77ab1f40f7a141032ef2edd9b5
Source dataset
uspto-grants-1988_07
Patent number
US04755215

Reaction notes

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