Hydrochloric Acid → HCID 22285033, compound

HRID 984849Notes

Reaction equation

HRID 984849 reaction equation
C[O:2][C:3]([C:5]1[C:14]([C:15]2[N:19]([CH3:20])[CH:18]=[N:17][CH:16]=2)=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO>[CH3:20][N:19]1[C:15]([C:14]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:16][N:17]=[CH:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20767729HCID 20767729, compound

Product 1

HCID 22285033HCID 22285033, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of methyl-3-(1-methyl-imidazol-5-yl)-2-naphthoate (Preparation 14) (8.5 g, 32 mmol) in THF/MeOH (3/2,120 mL) was treated with aqueous NaOH (1.0 N, 48 mL). After 20 hours at RT, it was neutralized with aqueous HCl (1.0 N, 20 mL). The solvent was evaporated in vacuo. The solid residue was treated with MeOH (5 mL), then evaporated again. The resulting crude material was purified by flash chromatography (5% MeOH/EtOAc) affording the title compound as a pale-yellow solid (6.0 g, 74%). 1H NMR (CDCl3): 8.34 (s, 1H), 7.95 (d, J=8.1, 1H), 7.90 (d, J=8.1, 1H), 7.72 (s, 1H), 7.53 (s, 1H), 7.52 (m, 1H), 7.50 (m, 1H), 6.83 (s, 1H), 3.16 (s, 3H). (ESI) m/z (M+H)+=253.10.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionThe solid residue was treated with MeOH (5 mL)
  3. customevaporated again
  4. customThe resulting crude material was purified by flash chromatography (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-31f25574684d4f05b34cfdd1b599d6b4
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Reaction notes

Loading…