Formaldehyde → HCID 67127833, compound

HRID 2040058Notes

Reaction equation

HRID 2040058 reaction equation
N#N.N[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[F:14])[C:7]([O:9][CH3:10])=[O:8].C=O.[BH3-][C:18]#[N:19].[Na+].[C:21]([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[CH3:21][N:19]([CH3:18])[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[F:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 947NitrogenHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 12541234Methyl 3-amino-4-fluorobenzoate

Product 1

HCID 67127833HCID 67127833, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of methyl 3-amino-4-fluorobenzoate (1.55 g, 9.16 mmol), paraformaldehyde (8.25 g, 91.63 mmol) and NaBH3CN (1.73 g, 27.49 mmol) was treated with acetic acid (90 mL) and the resulting mixture was stirred at rt for 4 h. Sat. aq. Na2CO3 was added to the reaction mixture and the pH was adjusted to 7-8. The mixture was extracted with CH2Cl2 (3×55 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 05c with a Waters Atlantis T3, 5 μm, 4.6×30 mm column: tR=0.76 min; [M+H]+=198.38.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×55 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-b71136d0b7d5483890c96253f7eabde4
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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