Water → HCID 73853099, compound

HRID 1246195Notes

Reaction equation

HRID 1246195 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]#[N:14])(=[O:3])[CH3:2].[OH2:15].C([O-])([O-])=O.[Na+].[Na+].[NH2:22]O.Cl>C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13](=[N:22][OH:15])[NH2:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 148193141-Acetyl-2,3-dihydro-1H-indole-2-carbonitrile

Product 1

HCID 73853099HCID 73853099, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-acetyl-2,3-dihydro-1H-indole-2-carbonitrile (0.0132 mole) was treated with water (54 ml) and the resulting suspension was treated sequentially with Na2CO3 (0.00726 mole) and NH2OH.HCl 0.0145 mole). The mixture was treated with ethanol (26 ml) and heated to 80–90° C. Upon achieving reaction temperature, the mixture was still a suspension. Added another 26 ml of ethanol which afforded a clear solution. The reaction was heated for 2.5 hours and cooled to room temperature with stirring. A voluminous precipitate formed which was collected by suction filtration, washed with cold distilled water, and air dried, yielding 2.23 g of 1-acetyl-2,3-dihydro-N′-hydroxy-1H-indole-2-carboximidamide (intermediate 14, mp. 204–205° C.).

Workup

  1. temperatureheated to 80–90° C
  2. customreaction temperature
  3. customafforded a clear solution
  4. temperatureThe reaction was heated for 2.5 hours
  5. customA voluminous precipitate formed which
  6. filtrationwas collected by suction filtration
  7. washwashed
  8. distillationwith cold distilled water, and air
  9. customdried

Sources & evidence

ORD record
ord-c4b60e12530144639bae718ae717de13
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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