Water → HCID 13784512, compound

HRID 1111249Notes

Reaction equation

HRID 1111249 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([NH:12][CH2:13][C:14]#[CH:15])=[CH:5][C:3]=1[NH2:4].[C:16]1(=O)[O:21][C:19](=[O:20])[C:18]2[CH2:22][CH2:23][CH2:24][CH2:25][C:17]1=2.O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([NH:12][CH2:13][C:14]#[CH:15])=[CH:5][C:3]=1[N:4]1[C:19](=[O:20])[C:18]2[CH2:22][CH2:23][CH2:24][CH2:25][C:17]=2[C:16]1=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13784511HCID 13784511, compound

Product 1

HCID 13784512HCID 13784512, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-fluoro-4-nitro-5-(2-propynylamino)-aniline (1.41 g) and 3,4,5,6-tetrahydrophthalic anhydride (1.33 g) was suspended in acetic acid (7 ml), followed by heating under reflux for 4 hours. The reaction mixture was cooled, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The extract was washed with water and an aqueous sodium bicarbonate solution, dried and concentrated to give 2-[2-fluoro-4-nitro-5-(2-propynylamino)phenyl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.85 g). m.p., 183.5° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionthe resultant mixture 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-0af0500da81e4153a8c9ff4bc3c21a0b
Source dataset
uspto-grants-1990_12
Patent number
US04978787

Reaction notes

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