Hydrochloric Acid → 3-Bromo-1,7-naphthyridin-8-ol

HRID 925467Notes

Reaction equation

HRID 925467 reaction equation
[CH3:1][N:2](C)/C=N/[H].[Br:7][C:8]1[CH:9]=[C:10]([CH3:17])[C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=1.CC([O-])(C)C.[K+].Cl>C1COCC1>[Br:7][C:8]1[CH:13]=[N:12][C:11]2[C:14](=[O:16])[NH:2][CH:1]=[CH:17][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 178422463HCID 178422463, compound

Product 1

HCID 895006083-Bromo-1,7-naphthyridin-8-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromo-3-methyl-pyridine-2-carboxylic acid 1-dimethylamino-meth-(E)-ylideneamine (2.5 g, 9.25 mmol) was dissolved in THF (20 ml). KOtBu (1.565 g, 13.05 mmol) in THF (30 ml) was added dropwise and the reaction mixture was heated to reflux for 3 h and then cooled to rt. The pH was adjusted to 7 with concentrated HCl. The reaction mixture was concentrated. The brown solid obtained was triturated with water (10 ml). The solid thus obtained was collected by filtration (2 g, 8 mmol).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. customThe brown solid obtained
  5. customwas triturated with water (10 ml)
  6. customThe solid thus obtained
  7. filtrationwas collected by filtration (2 g, 8 mmol)

Sources & evidence

ORD record
ord-dd2ef5341aad42e0b09cdc98011ef78a
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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