Acetic Acid → 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

HRID 1614292Notes

Reaction equation

HRID 1614292 reaction equation
C1(N[NH:8][C:9]2[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH:10]=2)C=CC=CC=1.S(=O)(=O)(O)O.[OH-].[Na+].[C:23](O)(=O)[CH3:24]>>[C:11]1(=[O:15])[C:10]2[C:24]3[CH:23]=[CH:11][CH:10]=[CH:9][C:14]=3[NH:8][C:9]=2[CH2:14][CH2:13][NH:12]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 197735285,6-Dihydro-4-(2-phenylhydrazino)-2(1H)-pyridinone

Product 1

HCID 156163232,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

Procedure

A solution of 5,6-dihydro-4-(2-phenylhydrazino)-2(1H)-pyridinone (8.0 g) in acetic acid (16 ml) was added over 30 min to concentrated sulphuric acid (16 ml) at 10°-20°. The reaction mixture was stirred for 2 h, then added over 10 min to 2N sodium hydroxide (150 ml) at 15°-25°. The solid product was filtered off, triturated with water (50 ml), then recrystallised from ethanol (20 ml) and dried in vacuo to give the title compound (3.79 g), m.p. 255°, t.l.c. (System B, 100:8:1) Rf 0.2.

Workup

  1. filtrationThe solid product was filtered off
  2. customtriturated with water (50 ml)
  3. customrecrystallised from ethanol (20 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-090f619c30dc4a279abf80b8da5c54d5
Source dataset
uspto-grants-1993_03
Patent number
US05196534

Reaction notes

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