Sodium Hydroxide → 6-[(Tert-butoxy)carbonyl]pyridine-3-carboxylic acid

HRID 354340Notes

Reaction equation

HRID 354340 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 543263102-Tert-butyl 5-methyl pyridine-2,5-dicarboxylate

Product 1

HCID 222714476-[(Tert-butoxy)carbonyl]pyridine-3-carboxylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 6-tert-butoxycarbonylnicotinate (1.2 g, 5.06 mmol) in THF (15 ml) and 0.25 N NaOH (40 ml, 10 mol) at an ambient temperature for 0.5 hr. The mixture was poured into ice-1N HCl (10 ml). The solid was collected, washed with water and air-died. The crude solid was recrystallized from CHCl3—EtOH—IPE to afford 6-tert-butoxycarbonylnicotinic acid (850 mg, 76%) as needles. IR (KBr) m/n 3095, 1728, 1705 cm−1; 1H-NMR (DMAO-d6) δ1.63 (s, 9 H), 8.09 (m, 1 H), 8.17 (m, 1 H), 8.42 (dt, J=2.4 and 8.3 Hz, 1 H), 9.21 (t, J=2.4 and 8.8 Hz, 1 H); MS (FAB) m/z 224 (M++1); Anal. Calcd. for C29H33N3O6: C, 36.18; H,3.18; N, 3.84. Found: C, 36.85; H, 3.35; N, 3.79.

Workup

  1. customThe solid was collected
  2. washwashed with water and air-died
  3. customThe crude solid was recrystallized from CHCl3—EtOH—IPE

Sources & evidence

ORD record
ord-edecde9e6879416195ecee6e3c2d276f
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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