Hydrochloric Acid → 2-Methoxypyrrolo[1,2-b]pyridazine-6-carboxylic acid

HRID 1748194Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9](C(OC)=O)=[C:10]([C:16]([O:18]C)=[O:17])[C:11]=2C(OC)=O)[N:8]=1.[OH-].[K+].Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[CH:11]=2)[N:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Trimethyl 2-methoxypyrrolo[1,2-b]pyridazine-5,6,7-tricarboxylate (1.84 g, 5.72 mmol) was suspended in a solution of potassium hydroxide (1.60 g, 28.6 mmol, 5 eq) in water (5 mL) and the mixture was heated to 60° C. for 1 h during which time all solids dissolved into a yellow solution. The solution was acidified with concentrated HCl (12 N, 5 mL) until pH=1 was achieved, and the mixture was heated to 90° C. overnight. The mixture was then cooled to RT and a dark solid was recovered by filtration. MS m/z 193.1 (M+1).

Workup

dissolutiondissolved into a yellow solution
temperaturethe mixture was heated to 90° C. overnight
temperatureThe mixture was then cooled to RT
filtrationa dark solid was recovered by filtration

Sources & evidence

ORD record: ord-cd2c1a9035734e13b43a5acdf3ed0a3e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150568B2

Reaction notes

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