Hydrochloric Acid → 4-(3-Azidopropoxy)-pyridine-2,6-dicarboxylic acid

HRID 495890Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])[CH:9]=[C:8]([C:19]([O:21]CC)=[O:20])[N:7]=1)=[O:5])C.[OH-].[Na+].Cl>O>[N:16]([CH2:15][CH2:14][CH2:13][O:12][C:10]1[CH:9]=[C:8]([C:19]([OH:21])=[O:20])[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:11]=1)=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 10 °C

Procedure

Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate, prepared above, (11.0 g, 34 mmol) was treated with a solution of sodium hydroxide (4.0 g, 0.10 mol) in water (120 mL) at 90-100° C. for 40 min. The reaction mixture was cooled to 10° C. and acidified to pH 1-2 with concentrated hydrochloric acid. The mixture was heated to dissolve the resulting white precipitate. Upon cooling 6.8 g (75%) of the title compound was obtained as white crystals.

Workup

temperatureThe mixture was heated
dissolutionto dissolve the resulting white precipitate

Sources & evidence

ORD record: ord-54e58c8bbbe74fbfbb4776192e44e116
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06942966B1

Reaction notes

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