Hydrochloric Acid → HCID 71087282, compound

HRID 1478904Notes

Reaction equation

HRID 1478904 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[N:4]([CH2:15][CH3:16])[CH:3]=1.Cl>CCO.[OH-].[Na+]>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]([CH2:15][CH3:16])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67353647HCID 67353647, compound

Product 1

HCID 71087282HCID 71087282, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3A, 3.0 g, 11 mmol) in EtOH (10 ml) and 1N NaOH (10 ml) was stirred at 80° C. for 5 days. The reaction mixture was acidified with 1N HCl, concentrated in vacuo and dried to give 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3B, 2.8 g, 10 mmol, 98% yield) as a pale brown powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (t, J=7.20 Hz, 3 H) 4.49 (q, J=7.33 Hz, 2 H) 8.35 (s, 1 H) 8.65 (s, 1 H) 8.91 (s, 1 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customdried

Sources & evidence

ORD record
ord-f6a1385c58a349ec94a3673a7860ee85
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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