Water → HCID 178473715, compound

HRID 887915Notes

Reaction equation

HRID 887915 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](=[NH:22])[NH:14][OH:15])(=[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 178473715HCID 178473715, 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 stiffing. 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 with stiffing
  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-a98330b2c1a1431cafffbafed04e3dd0
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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