Water → HCID 12944312, compound

HRID 436163Notes

Reaction equation

HRID 436163 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][CH:13]3[C:18]#[N:19])=[O:8])=[CH:3][CH:2]=1.[OH2:21]>>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][CH:13]3[C:18]([NH2:19])=[O:21])=[O:8])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 962WaterHCID 20310091HCID 20310091, compound

Product 1

HCID 12944312HCID 12944312, compound

Conditions

Temperature
90 °C

Procedure

To 2.3 g. of 4-(p-toluoyl)indan-1-carbonitrile is added 75 g. of polyphosphoric acid and the mixture is worked into a homogeneous solution by heating on a water bath at 90° C for 30 minutes and, then, on an oil bath at 120°-130° C for 30 minutes. Following the addition of water to decompose the polyphosphoric acid, the reaction mixture is extracted with ethyl acetate. The extract is washed with water, 5 % aqueous sodium hydrogen carbonate and water in the order mentioned and, then, dried. It is, then, treated with activated carbon and concentrated under reduced pressure. The resultant crystalline residue is recrystallized from a mixture of ethanol and ethyl acetate. The described procedure gives 4-(p-toluoyl)indan-1-carboxamide as crystals melting at 188°-191° C.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. washThe extract is washed with water, 5 % aqueous sodium hydrogen carbonate and water in the order
  3. customdried
  4. additiontreated with activated carbon
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crystalline residue is recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-f77debd814fe49ca81bef220d47cb14e
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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