Hydrochloric Acid → 1-Nitrosoindoline

HRID 1894739Notes

Reaction equation

HRID 1894739 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N:10]([O-])=[O:11].[Na+].Cl>C(O)(=O)C.O>[N:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10328IndolineHCID 23668193Sodium Nitrite

Product 1

HCID 242741-NitrosoindolineYield 42.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2,3-dihydro-1H-indole (10.0 g, 84 mmol) in acetic acid (100 ml) at 0° C. was added dropwise a solution of sodium nitrite (6.08 g, 88 mmol) in water (25 ml) so that the temperature was maintained below 5° C. After 1 hour water (500 ml) and 1 M hydrochloric acid (500 ml) were added to the precipitate that formed. The mixture was stirred for another hour before the product was filtered off, washed with water (3×100 ml) and dried under vacuum to give 1-nitroso-2,3-dihydro-1H-indole as a brown solid (5.27 g). 400 MHz 1H NMR (DMSO-d6) δ: 7.8 (d, J=7.6 Hz 1H), 7.45 (d, J=7.6 Hz, 1H), 7.37 (t, J=7.6 Hz 1H), 7.29 (t, J=7.6 Hz, 1H), 4.09 (m, 2H), 3.19 (t, J=7.6 Hz, 2H); LCMS: 149 [M+H]

Workup

  1. temperaturewas maintained below 5° C
  2. customthat formed
  3. filtrationwas filtered off
  4. washwashed with water (3×100 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e70b2a533e494b7f94fb6c8ee458c488
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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