Sulfuric Acid → HCID 23671997, compound

HRID 1875484Notes

Reaction equation

HRID 1875484 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Na+:11].[Cl-].[S:13](=O)(=[O:16])([OH:15])[OH:14]>>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:13]([O-:16])(=[O:15])=[O:14])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Na+:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 23671997HCID 23671997, compound

Conditions

Temperature
100 °C

Procedure

1,2,3,4-tetrahydroquinoline was added dropwise to 40 mL fuming sulfuric acid at 0° C. over 15 minutes. This mixture was then heated to 100° C. for 1 hour with stirring. After cooling to 0° C. saturated NaCl (aqueous) was added drop wise, precipitating the crude product as a white solid. The solid was washed, first with cold isopropanol, followed by diethyl ether, then dried under vacuum to give the desired product as a white solid. 1H-NMR (300 MHz, d6 DMSO): δ 7.43 (m, 2H), 7.21 (d, 1H), 3.38 (m, 2H), 2.81 (t, 2H) 1.96 (m, 2H) ppm; MS m/z calculated for C9H10NO3S (M−): 212.04. Found 212.0 (M−, ESI−).

Workup

  1. additionwas added drop wise
  2. customprecipitating the crude product as a white solid
  3. washThe solid was washed, first with cold isopropanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9f160842d7cf47fea03b0c3cf67f89e1
Source dataset
uspto-grants-2012_11
Patent number
US08309059B2

Reaction notes

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