Tetraethyl 5,5'-(1,8-naphthyridine-2,7-diyl)diisophthalate → 5,5'-(1,8-Naphthyridine-2,7-diyl)diisophthalic acid

HRID 1484218Notes

Reaction equation

HRID 1484218 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([C:22]([O:24]CC)=[O:23])[CH:14]=[C:15]([CH:21]=3)[C:16]([O:18]CC)=[O:17])[N:9]=2)[CH:4]=[CH:3][C:2]=1[C:27]1[CH:28]=[C:29]([C:38]([O:40]CC)=[O:39])[CH:30]=[C:31]([CH:37]=1)[C:32]([O:34]CC)=[O:33]>C1COCC1.CO.[OH-].[Na+]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:21]=[C:15]([C:16]([OH:18])=[O:17])[CH:14]=[C:13]([CH:12]=3)[C:22]([OH:24])=[O:23])[N:9]=2)[CH:4]=[CH:3][C:2]=1[C:27]1[CH:37]=[C:31]([C:32]([OH:34])=[O:33])[CH:30]=[C:29]([CH:28]=1)[C:38]([OH:40])=[O:39]

Participants

5

Reactant 1

HCID 117940372Tetraethyl 5,5'-(1,8-naphthyridine-2,7-diyl)diisophthalate

Product 1

HCID 706984375,5'-(1,8-Naphthyridine-2,7-diyl)diisophthalic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.0 g of tetraethyl 5,5′-(1,8-naphthyridine-2,7-diyl)diisophthalate was dissolved in 60 mL of mixed solvent of THF and MeOH (v/v=1:1), 20 mL of 2N NaOH aqueous solution was added. The mixture was stirred at room temperature overnight. After the organic phase was removed, the aqueous phase was acidified with dilute hydrochloric acid to give white precipitate, which was filtered and washed with water several times. Yield: 1.5 g, 94%. 1H NMR (300 MHz, DMSO-d6): δ 8.44 (d, 2H), 8.62 (s, 2H), 8.68 (d, 2H), 9.10 (s, 4H).

Workup

  1. additionwas added
  2. customAfter the organic phase was removed
  3. customto give white precipitate, which
  4. filtrationwas filtered
  5. washwashed with water several times

Sources & evidence

ORD record
ord-9af959f2d5604b48a87bb48424671ff9
Source dataset
uspto-grants-2016_08
Patent number
US09421514B2

Reaction notes

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