Sulfuric Acid → HCID 89618025, compound

HRID 1502574Notes

Reaction equation

HRID 1502574 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]([CH2:19][C:20]([O:22][CH2:23]C)=[O:21])(C(OCC)=O)[C:8]2=[O:25])=[O:4].Cl.C(O)(=O)C.C(CC1C(=O)C2C(=CC=C(C(O)=O)C=2)C1)(O)=O.S(=O)(=O)(O)O>CO>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH:9]1[C:8](=[O:25])[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 22641269Acetate-hydrochloric acidHCID 89618008HCID 89618008, compoundHCID 89618089HCID 89618089, compound

Product 1

HCID 89618025HCID 89618025, compoundYield 686.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Ethoxycarbonylmethyl-3-oxo-indan-2,5-dicarboxylic acid-2-ethyl ester-5-methyl ester (Step 2, 530 mg, 1.5 mmol) in 1.3 ml mixture of 6 N HCl: acetic acid (1:1) was heated to reflux for 3 h. The reaction mixture was evaporated to dryness, 10 ml water was added and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and then concentrated. The crude product was washed with hexane and precede next step without further purification (530 mg). To a stirred solution of 2-carboxymethyl-3-oxo-indan-5-carboxylic acid (3.5 g, 14.9 mmol) in methanol (53 ml) was added concentrated sulphuric acid (5.6 ml) at 0° C. After addition temperature of the reaction mixture was slowly raised to room temperature and then heated to reflux for 5 h. The reaction mixture was evaporated. Water was added and extracted with ethyl acetate. Ethyl acetate layer was washed with saturated aqueous sodium bicarbonate, brine, dried and concentrated under reduced pressure. Crude was purified by column chromatography using acetone/hexane (25%) to yield a desired product (2.7 g). 1H NMR (400 MHz, CDCl3) d 8.44 (1H, s), 8.30 (1H, d), 7.57 (1H, d), 3.95 (3H, s), 3.78 (3H, s), 3.53 (1H, dd), 3.09-2.93 (3H, m), 2.71 (1H, dd) ppm.

Workup

  1. temperatureto reflux for 3 h
  2. customThe reaction mixture was evaporated to dryness, 10 ml water
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washOrganic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. washThe crude product was washed with hexane
  9. customwithout further purification (530 mg)
  10. additionAfter addition temperature of the reaction mixture
  11. temperatureheated
  12. temperatureto reflux for 5 h
  13. customThe reaction mixture was evaporated
  14. additionWater was added
  15. extractionextracted with ethyl acetate
  16. washEthyl acetate layer was washed with saturated aqueous sodium bicarbonate, brine
  17. customdried
  18. concentrationconcentrated under reduced pressure
  19. customCrude was purified by column chromatography

Sources & evidence

ORD record
ord-e5f0fa803e4b48098d782e160c825f59
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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