Hydrochloric Acid → HCID 86691930, compound

HRID 717780Notes

Reaction equation

HRID 717780 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]2.Cl.[N:18]([O-])=[O:19].[Na+]>C(O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:18]=[O:19])[CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4566228HCID 4566228, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86691930HCID 86691930, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5-Methyl-2-phenylindoline (0.7 g, 0.00334 mol) was dissolved in ethanol (5 mL), and 1N hydrochloric acid solution (3.5 mL) was added at 0° C. The resulting reaction mixture was stirred for 5 min, and then a solution of sodium nitrite (0.462 g, 0.00668 mol) in water (8.5 mL) was added at 0° C. The mixture was stirred for 1 h at RT, and after completion of reaction (monitored by TLC), the solvent was removed under reduced pressure to obtain product as a brown colored oil (0.8 g).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe mixture was stirred for 1 h at RT
  3. customafter completion of reaction (monitored by TLC)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f8034ca9b2874a069e94dc3e633d7d42
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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