Hydrochloric Acid → 4,7-Dihydro-4,7-dioxo-6-methoxy-1-methyl-1H-cyclohepta[b]pyridine-2-carboxylic Acid

HRID 66137Notes

Reaction equation

HRID 66137 reaction equation
C([O:3][C:4]([C:6]1[N:11]([CH3:12])[C:10]2[CH:13]=[CH:14][C:15](=[O:20])[C:16]([O:18][CH3:19])=[CH:17][C:9]=2[C:8](=[O:21])[CH:7]=1)=[O:5])C.[OH-].[K+].Cl>>[O:21]=[C:8]1[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[N:11]([CH3:12])[C:10]2[CH:13]=[CH:14][C:15](=[O:20])[C:16]([O:18][CH3:19])=[CH:17][C:9]1=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 536442194,7-dihydro-4,7-dioxo-6-methoxy-1-methyl-1H-cyclohepta[b]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 227555974,7-Dihydro-4,7-dioxo-6-methoxy-1-methyl-1H-cyclohepta[b]pyridine-2-carboxylic Acid

Procedure

A mixture of 4,7-dihydro-4,7-dioxo-6-methoxy-1-methyl-1H-cyclohepta[b]pyridine-2-carboxylic acid ethyl ester (2.89 g, described in Example 7) and 1N potassium hydroxide (11 ml) is stirred at room temperature for 16 hr. Hydrochloric acid (10%) is added until the solution is acidic. The precipitate is collected, washed with water and acetone and crystallized from acetic acid to obtain crystals of the title compound, mp > 250° C.

Workup

  1. customThe precipitate is collected
  2. washwashed with water and acetone
  3. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-c466c3a258e14e62a3800a0fa5fddc87
Source dataset
uspto-grants-1978_12
Patent number
US04130649

Reaction notes

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