Hydrochloric Acid → HCID 178509486, compound

HRID 447431Notes

Reaction equation

HRID 447431 reaction equation
[N:1]([O-])=O.[Na+].[C:5]([C:7]1[CH:15]=[C:14]2[C:10](C=C[NH:13]2)=[CH:9][CH:8]=1)#[N:6].Cl.CCO[C:20]([CH3:22])=[O:21]>O>[CH:20]([C:22]1[C:10]2[C:14](=[CH:15][C:7]([C:5]#[N:6])=[CH:8][CH:9]=2)[NH:13][N:1]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 851461H-indole-6-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178509486HCID 178509486, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of NaNO2 (11.04 g, 160 mmol) in H2O (200 mL) was added 6-cyanoindole (5.68 g, 40 mmol) in one portion slowly. The resulting suspension was stirred for 5 min at rt. HCl (32 mL, 192 mmol 6N) was added dropwise via a dropping funnel over 30 min and the pH was about 1. The resulting suspension was stirred for 4.5 h at rt before of EtOAc (400 mL) was added. After stirring for additional 10 min to dissolve the precipitate, the two layers were separated and the aqueous layer was extracted with EtOAc (150 mL). Combined extracts were dried over Na2SO4. Removal of solvents afforded 6.864 g (100%) of title compound as brown (coffee color) solid. 1H NMR (400 MHz, DMSO-d6) δ 14.70 (s, 1H, NH), 10.22 (s, 1H, CHO), 8.38 (s, 1H), 8.28 (d, J=8.4 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H). MS ESI 172.0 [M+H]+, calcd for [C9H5N3O+H]+ 172.0.

Workup

  1. additionwas added
  2. stirringAfter stirring for additional 10 min
  3. dissolutionto dissolve the precipitate
  4. customthe two layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (150 mL)
  6. dry with materialCombined extracts were dried over Na2SO4
  7. customRemoval of solvents

Sources & evidence

ORD record
ord-c1080a3f06f24ffaa12e420c2d6f8d1e
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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