Water → HCID 14515321, compound

HRID 1646611Notes

Reaction equation

HRID 1646611 reaction equation
[OH:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3]1.[C:13](OC(=O)C)(=[O:15])[CH3:14].O.[Cl-].[Na+]>N1C=CC=CC=1>[C:13]([O:1][CH:2]1[C:10]2[C:5](=[C:6]([C:11]#[N:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 145153071-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile

Product 1

HCID 14515321HCID 14515321, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

3.89 g of (RS) 1-hydroxy-4-indanecarbonitrile in 39 ml of pyridine is cooled to 0° C., 3.45 ml of acetic anhydride is added drop by drop, and the whole is agitated for 16 hours at 20° C. The reaction mixture is poured into 300 ml of water containing sodium chloride and extracted with isopropyl ether; the ethereal phase is washed with 2N hydrochloric acid and then with water until pH 7 is obtained. The ethereal phase is dried and brought to dryness, and the residue is taken up in 1,2-dichloroethane, and again concentrated to dryness under reduced pressure. The residue is taken up in 40 ml of hexane, agitated for one hour, filtered, and 4.46 g of expected product is recovered. M.p.=65° C.

Workup

  1. extractionextracted with isopropyl ether
  2. washthe ethereal phase is washed with 2N hydrochloric acid
  3. customwith water until pH 7 is obtained
  4. customThe ethereal phase is dried
  5. concentrationagain concentrated to dryness under reduced pressure
  6. stirringagitated for one hour
  7. filtrationfiltered
  8. custom4.46 g of expected product is recovered

Sources & evidence

ORD record
ord-3850c29e98214609b29db6044ddbfd73
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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