Formaldehyde → HCID 23356529, compound

HRID 233465Notes

Reaction equation

HRID 233465 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.C=O.[OH-].[Na+].[C:15](=O)(O)[O-:16].[Na+]>O.Cl>[OH:16][CH2:15][C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]2=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5834321-Methylpyrrolo[1,2-a]pyrazine

Product 1

HCID 23356529HCID 23356529, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3 g (22.7 mmol) of 1-methylpyrrolo[1,2-a]pyrazine prepared in Preparation Example 2 was dissolved in water (15 ml)/concentrated hydrochloric acid (35 ml) mixture while cooling with ice-water. The resulting solution was heated to 70° C.; and 60 ml of formalin was added dropwise thereto over 40 minutes. The resulting solution was stirred at 75° C. for 30 minutes, cooled to 0° C. and then neutralized to pH8.0 with sodium hydroxide and sodium bicarbonate. The reaction mixture was extracted with ethyl acetate (100 ml×3), dried over MgSO4 and then concentrated. The residue was chromatographed over silica gel to obtain 1.8 g of title compound (yield: 48.9%).

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe reaction mixture was extracted with ethyl acetate (100 ml×3)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-8b5b3af7b4b94255a3343325235e3156
Source dataset
uspto-grants-1997_01
Patent number
US05593984

Reaction notes

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