Hydrochloric Acid → HCID 178513279, compound

HRID 717732Notes

Reaction equation

HRID 717732 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]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[C:4]2[CH:5]=[CH:6][NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1)=[NH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10340Sodium CarbonateHCID 38176024-Cyanoindole

Product 1

HCID 178513279HCID 178513279, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 4-cyanoindole (0.64 g; 4.5 mmol), HCl×H2NOH (1.1 g; 15.8 mmol), and Na2CO3 (0.79 g; 7.43 mmol) in H2O (8 ml) and EtOH (2 ml) was gently stirred for 15 min, then refluxed for 6 h under N2. After cooling most of the EtOH was removed under reduced pressure and the product was extracted with EtOAc (3×10 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 (0.74 g; 94%), as a creamy foam. 1H-NMR (DMSO-d6+CDCl3+CD3OD) 7.4-7.3 (m, 1H); 7.2-7.12 (m, 2H); 7.01 (t, 1H, J=7.8 Hz); 6.74 (d, 1H, J=3.1 Hz); 3.68 (HDO); 1.71 (broad s, H2O).

Workup

  1. temperaturerefluxed for 6 h under N2
  2. customwas removed under reduced pressure
  3. extractionthe product was extracted with EtOAc (3×10 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-e65859653b294f92be7f1c0770b8fbfb
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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