Acetyl chloride → 7-Nitroisochroman-1,3-dione

HRID 2170122Notes

Reaction equation

HRID 2170122 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:13][C:14]([OH:16])=[O:15])=[C:8]([CH:12]=1)[C:9]([OH:11])=O)([O-:3])=[O:2].C(Cl)(=O)C>>[N+:1]([C:4]1[CH:12]=[C:8]2[C:7]([CH2:13][C:14](=[O:15])[O:16][C:9]2=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 123034522-(Carboxymethyl)-5-nitrobenzoic acid

Product 1

HCID 118306067-Nitroisochroman-1,3-dione

Procedure

A oven-dried 10 mL round-bottomed flask containing a stirring bar was charged with 5-nitro-2-(carboxymethyl)benzoic acid (500 mg, 2.22 mmol). Freshly distilled acetyl chloride (5.0 ml) was added, the flask was fitted with a condenser and the reaction mixture was refluxed under an argon atmosphere for 16 h. The reaction was then cooled to room temperature and the excess acetyl chloride was removed in vacuo. The solid obtained was triturated with Et2O (5.0 mL), filtered and dried to give 7-nitroisochroman-1,3-dione as an off white solid (372.5 mg, 81%). Spectral data for this compound were consistent with those in the literature. M.p. 154-156° C. (lit. m.p. 154-155° C.); 1H NMR (400 MHz, DMSO-d6): δ=8.67 (s, 1H), 8.54 (d, J=7.5 Hz, 1H), 7.72 (d, J=7.5 Hz, 1H), 4.41 (s, 2H).

Workup

  1. additionA oven-dried 10 mL round-bottomed flask containing a stirring bar
  2. customthe flask was fitted with a condenser
  3. temperaturethe reaction mixture was refluxed under an argon atmosphere for 16 h
  4. customthe excess acetyl chloride was removed in vacuo
  5. customThe solid obtained
  6. customwas triturated with Et2O (5.0 mL)
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-bb6f66de93fc4fdfbf31bc16cb351190
Source dataset
uspto-grants-2015_06
Patent number
US09050586B2

Reaction notes

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