Formaldehyde → HCID 68676574, compound

HRID 2233010Notes

Reaction equation

HRID 2233010 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][NH:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C=O.[C:14](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:14][N:3]1[C:8]2[C:9](=[CH:4][CH:5]=[CH:6][N:7]=2)[CH:10]=[CH:11][CH:2]1[Cl:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 184491662-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 68676574HCID 68676574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 250 mg of 2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (U.S. Pat. No. 6,169,093) in methylene chloride (6.1 mL) was treated with 0.148 mL of a 37% formalin solution, followed by 0.388 g of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 60 h and quenched by the addition of 2N sodium hydroxide (6 mL). After stirring for one h, the mixture was diluted with water and extracted with methylene chloride (2×). The organic layers were dried over sodium sulfate, filtered, and concentrated. Purification of the residue using silica gel chromatography provided N-methylchloronaphthyridine.

Workup

  1. customquenched by the addition of 2N sodium hydroxide (6 mL)
  2. stirringAfter stirring for one h
  3. additionthe mixture was diluted with water
  4. extractionextracted with methylene chloride (2×)
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue

Sources & evidence

ORD record
ord-d2199fbac5754057ae005f030d3d2c27
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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