Hydrochloric Acid → 2-(Acetylmethyl)-3-fluoro-4-phthalimidonitrobenzene

HRID 2222426Notes

Reaction equation

HRID 2222426 reaction equation
C[O:2][C:3](OC)([CH3:26])[CH2:4][C:5]1[C:10]([F:11])=[C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH:8]=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24].Cl>C1COCC1.CO>[C:3]([CH2:4][C:5]1[C:10]([F:11])=[C:9]([N:12]2[C:13](=[O:22])[C:14]3=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]3[C:16]2=[O:17])[CH:8]=[CH:7][C:6]=1[N+:23]([O-:25])=[O:24])(=[O:2])[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 591066082-(2,2-Dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene

Product 1

HCID 591066072-(Acetylmethyl)-3-fluoro-4-phthalimidonitrobenzeneYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2,2-Dimethoxypropyl)-3-fluoro-4-phthalimidonitrobenzene (5.5 g, 14 mmol) was suspended in a mixture of THF (200 ml) and methanol (100 ml). HCl 2N (1 ml) was added and the mixture was stirred at ambient temperature for 30 minutes. The solvents were evaporated off and the residue redissolved in methylene chloride, dried (MgSO4), filtered and the solvent evaporated off. The residue was triturated in pentane and collected by filtration to give 2-(acetylmethyl)-3-fluoro-4-phthalimidonitrobenzene (4.8 g, 100%) as a pale yellow solid.

Workup

  1. customThe solvents were evaporated off
  2. dissolutionthe residue redissolved in methylene chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated off
  6. customThe residue was triturated in pentane
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-cec5f6f6f7c2455b957327488e7e4838
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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