HCID 13784512, compound → HCID 15595972, compound

HRID 1200260Notes

Reaction equation

HRID 1200260 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)amino-phenyl]-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-ad97765e46634ec08352a08a489c05e1
Source dataset
uspto-grants-1990_02
Patent number
US04904800

Reaction notes

Loading…