Sulfuric Acid → 1,1,2-Trimethyl-1H-benzo[e]indole-7-sulfonic acid

HRID 2106987

Reaction equation

HRID 2106987 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:15].[OH:17][S:18](O)(=[O:20])=[O:19]>[OH-].[Na+]>[S:18]([C:13]1[CH:12]=[CH:11][C:9]2[C:10]3[C:2]([CH3:16])([CH3:1])[C:3]([CH3:15])=[N:4][C:5]=3[CH:6]=[CH:7][C:8]=2[CH:14]=1)([OH:20])(=[O:19])=[O:17]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 1705302,3,3-Trimethylbenzoindolenine

Product 1

HCID 198472691,1,2-Trimethyl-1H-benzo[e]indole-7-sulfonic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

1,1,2-Trimethyl-1H-benz[e]indole, 100 g. was added with stirring to 500 mL of concentrated H2SO4. The mixture was heated at 180° C. for 1/2 h, cooled to 60° C. and poured onto 2 Kg ice. Cautionsly 500 ml of 50% aqueous NaOH was added. After 24 hours at room temperature the solid was filtered off, and 500 mL of saturated aqueous Na2SO4 was added. The resulting solid precipitate was collected, added to the previously filtered solid, and recrystallized from 2 L of H2O. Yield 25 g after overnight vacuum drying at 50° C. The location of the sulfo group was determined as being the 7-position by proton nuclear magnetic resonance measurements.

Workup

  1. additionwas added
  2. temperaturecooled to 60° C.
  3. filtrationAfter 24 hours at room temperature the solid was filtered off
  4. addition500 mL of saturated aqueous Na2SO4 was added
  5. customThe resulting solid precipitate was collected
  6. additionadded to the previously filtered solid
  7. customrecrystallized from 2 L of H2O
  8. customYield 25 g after overnight vacuum drying at 50° C

Sources & evidence

ORD record
ord-cd0326d55861465aa217f15243fad443
Source dataset
uspto-grants-1990_06
Patent number
US04933269

Linked notes

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