Water → HCID 73853099, compound

HRID 551393Notes

Reaction equation

HRID 551393 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×

Conditions

Temperature
85 °C

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. customreaction temperature
  2. customafforded a clear solution
  3. temperatureThe reaction was heated for 2.5 hours
  4. temperaturecooled to room temperature
  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-09e4ac5ee9f54e9d9d74b6a47df9abf8
Source dataset
uspto-grants-2011_05
Patent number
US07947713B2

Reaction notes

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