Benzyl Bromide → 5-[(Benzyloxy)carbonyl]nicotinic acid

HRID 860473

Reaction equation

[H-].[Na+].[N:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([C:12]([OH:14])=[O:13])[CH:4]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:10][C:9]([C:7]1[CH:8]=[N:3][CH:4]=[C:5]([CH:6]=1)[C:12]([OH:14])=[O:13])=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 60% sodium hydride (527 mg) in dimethylformamide (20 mL) was added 3,5-pyridinedicarboxylic acid (2.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. To the mixture was added (bromomethyl)benzene (2.05 g) and the mixture was stirred at 60° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with ethyl acetate to give 5-[(benzyloxy)carbonyl]nicotinic acid as a pale yellow powder (722 mg).

Workup

stirringthe mixture was stirred at 60° C. for 2 hours
customThe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-73d806606503471c8e06e8a873b009fc
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Linked notes

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