Formic Acid → HCID 178526913, compound

HRID 532702Notes

Reaction equation

HRID 532702 reaction equation
O.[N+:2]([CH:5]([CH:8]=O)[CH:6]=O)([O-:4])=[O:3].[Na].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)=O>CN(C=O)C.O>[CH2:11](/[N:18]=[CH:6]/[CH:5]([N+:2]([O-:4])=[O:3])/[CH:8]=[N:18]/[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7504BenzylamineHCID 71317419Sodium nitromalonaldehyde hydrate

Product 1

HCID 178526913HCID 178526913, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent2×

Procedure

A turbid, yellow-orange solution of sodium nitromalonaldehyde monohydrate (15.7 mg, 0.10 mmol) in DMF (275 uL) and water (25 uL) was added dropwise over a 2 min period to a solution of benzylamine (27.4 uL, 0.25 mmol) in DMF (165 uL), water (15 uL) and 96% formic acid (0.94 uL, 0.025 mmol) and was stirred at room-temperature for 24 h. A few drops of the reaction mixture were added to ˜1 mL water giving a white, opaque emulsion that was extracted with EtOAc twice. The combined organics were dried over Na2SO4, evaporated under N2 and dried in vacuo at room-temperature to give 3.0 mg of the crude title compound (I1) as a pale-pink residue (3.0 mg, 10% crude yield); HRMS calcd for C17H18N3O2 (M+H+) 296.13990, obsd 296.13733 (100%); 1H NMR (300 MHz, DMSO-d6) δ 4.719 (s, 4H), 7.274-7.304 (m, 10H), 8.898 (s, 2H), ˜11.7 (br s, 1H).

Workup

  1. extractionwas extracted with EtOAc twice
  2. dry with materialThe combined organics were dried over Na2SO4
  3. customevaporated under N2
  4. customdried in vacuo at room-temperature

Sources & evidence

ORD record
ord-6372fd07e6d44813aa78d81f8ce757f0
Source dataset
uspto-grants-2014_10
Patent number
US08853220B1

Reaction notes

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