Sodium Hydroxide → 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylic acid

HRID 2410681Notes

Reaction equation

HRID 2410681 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH:13]=[C:12]([C:24]([O:26]C)=[O:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[CH:13]=[C:12]([C:24]([OH:26])=[O:25])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66604714methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

Product 1

HCID 666050157-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole -4-carboxylate (150 mg, 0 4 mmol) was dissolved in a mixture of tetrahydrofuran (6 mL) and methanol (2 mL) and an aqueous solution of sodium hydroxide (1.0 N, 1.8 mL, 1.8 mmol) was added. After 1 hr the organic solvents were removed on the rotary evaporator and the pH of the aqueous solution was adjusted to about 3 with 6 N aqueous HCl. The resulting precipitate was collected by filtration, washed with water, and dried under vacuum in the presence of KOH to leave 7-methoxy-2-(4-methoxyphenyl)-5H -pyrido[3,2-b]indole-4-carboxylic acid (138 mg, 67% yield) as an orange solid. MS (ESI) m/z 349.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.47 (1H, s), 8.18 (1H, d, J=8.55 Hz), 8.16 (1H, s), 8.13 (2H, d, J=8.55 Hz), 7.29 (1H, d, J=1.83 Hz), 7.10 (2H, d, J=8.85 Hz), 6.94 (1H, dd, J=8.55, 1.83 Hz), 3.89 (3H, s), 3.85 (3H, s).

Workup

  1. customAfter 1 hr the organic solvents were removed on the rotary evaporator
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialdried under vacuum in the presence of KOH

Sources & evidence

ORD record
ord-cd4916364c414bb89b7948579b23b602
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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