Sodium Hydroxide → HCID 69309518, compound

HRID 2217753Notes

Reaction equation

HRID 2217753 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[N:23]=[CH:22][C:11]2[N:12]([CH:19]([CH3:21])[CH3:20])[C:13]3[C:18]([C:10]=2[CH:9]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:7])C>CO.O>[C:6]([C:8]1[N:23]=[CH:22][C:11]2[N:12]([CH:19]([CH3:20])[CH3:21])[C:13]3[C:18]([C:10]=2[CH:9]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 693078463-Ethoxycarbonyl-9-isopropyl-9H-pyrido[3,4-b]indole

Product 1

HCID 69309518HCID 69309518, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution (1 mol dm−3) of sodium hydroxide (21 ml, 21 mmol) was added over 10 minutes to a stirred solution of 3-ethoxycarbonyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 1; 2.9 g, 10.3 mmol) in a MeOH/water mix (100 ml 2:1 v/v), and the mixture was allowed to stir for 20 hours at room temperature. MeOH was removed in vacuo and the mixture acidified by the addition of HCl (1 mol dm−3). The precipitate was filtered, washed with water and dried under vacuum at 65° C. for 2 hours to give a light yellow solid (2.15 g). NMR (300 MHz) 9.19 (s, 1H), 8.91 (s, 1H), 8.41 (d, 1H), 7.85 (d, 1H), 7.62 (t, 1H), 7.31 (t, 1H), 5.26 (m, 1H), 1.66 (d 6H); m/z 255.

Workup

  1. additionmix (100 ml 2:1 v/v)
  2. customMeOH was removed in vacuo
  3. additionthe mixture acidified by the addition of HCl (1 mol dm−3)
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried under vacuum at 65° C. for 2 hours

Sources & evidence

ORD record
ord-1ec7af8aee8945609db804bff63b2f0c
Source dataset
uspto-grants-2008_08
Patent number
US07408064B2

Reaction notes

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