Hydrochloric Acid → HCID 21914108, compound

HRID 887912Notes

Reaction equation

HRID 887912 reaction equation
Cl.[C:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:15]#[N:16])(=[O:4])[CH3:3].[CH2:17]([OH:19])[CH3:18]>C(OCC)C>[ClH:14].[C:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:15](=[NH:16])[O:19][CH2:17][CH3:18])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid4×HCID 702EthanolHCID 21914138HCID 21914138, compound

Product 1

HCID 21914108HCID 21914108, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

HCl (as a 2 M solution) was added slowly to intermediate (9) until gas evolution was noted. Then stopped adding the prepared HCl (2N in diethylether), and suspended HCl in diethylether (150 ml) and then ethanol (0.042 mole) was added. The mixture was cooled to 0° C. and HCl (gas) was added over an hour, with an oil precipitating out. The reaction was diluted to 1 l with diethylether. More oil precipitates, and no solid formed after sitting for 1 hour. The diethylether was decanted off. The residue was diluted (diethylether, 500 ml). The solid begins to form, and the mixture was stirred for 2 hours. The sample was filtered, rinsing with diethylether. The sample was placed under vacuum, yielding 6.41 g of ethyl 1-acetyl-5-chloro-2,3-dihydro-1H-indole-2-carboximidate monohydrochloride (intermediate 10).

Workup

  1. customprecipitating out
  2. additionThe reaction was diluted to 1 l with diethylether
  3. customMore oil precipitates
  4. customno solid formed
  5. customThe diethylether was decanted off
  6. additionThe residue was diluted (diethylether, 500 ml)
  7. customto form
  8. filtrationThe sample was filtered
  9. washrinsing with diethylether

Sources & evidence

ORD record
ord-656ef62754f34543aaabc922dd894efa
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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