Hydrochloric Acid → HCID 178513238, compound

HRID 710295Notes

Reaction equation

HRID 710295 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].Cl.[NH2:13][OH:14].C([O-])([O-])=O.[Na+].[Na+]>O.CCO>[OH:14][NH:13][C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=[NH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10340Sodium CarbonateHCID 27513Indole-5-carbonitrile

Product 1

HCID 178513238HCID 178513238, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of the product of Step A (0.2 g; 1.41 mmol), HCl×H2NOH (0.36 g; 5.2 mmol), and Na2CO3 (0.26 g; 2.44 mmol) in H2O (8 ml) and EtOH (2 ml) was gently stirred for 10 min, then refluxed overnight under N2. After cooling most of the ethanol was removed under reduced pressure and the product was extracted with EtOAc (20 ml). The organic phase was separated, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.23 g; 92%), as a creamy foam. 1H-NMR (CDCl3+CD3OD) 1.71 (broad s, H2O); 4.93* (broad s, 0.5H); 6.55 (d, 1H, J=3 Hz); 7.21 (d, 1H, J=3 Hz); 7.28-7.42 (m, 2H); 7.87 (d, 1H, J=1 Hz); 8.63* (broad s, 0.3H).

Workup

  1. temperaturerefluxed overnight under N2
  2. customwas removed under reduced pressure
  3. extractionthe product was extracted with EtOAc (20 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-10a6045b0c9842fe9a7768a2d8296352
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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