Formic Acid → HCID 178491095, compound

HRID 532703Notes

Reaction equation

HRID 532703 reaction equation
O.[N+:2]([CH:5]([CH:8]=O)[CH:6]=O)([O-:4])=[O:3].[Na].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.[CH:21]([OH:23])=O>CO.O>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]/[N:18]=[CH:8]/[CH:5]([N+:2]([O-:4])=[O:3])/[CH:6]=[N:18]/[CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:23][CH3:21])=[CH:14][CH:15]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 754524-MethoxybenzylamineHCID 71317419Sodium nitromalonaldehyde hydrate

Product 1

HCID 178491095HCID 178491095, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

A yellow-orange suspension of sodium nitromalonaldehyde monohydrate (15.7 mg, 0.10 mmol) in methanol (275 uL) and water (25 uL) was added dropwise over a 2 min period to a solution of 4-methoxybenzylamine in methanol (165 uL), water (15 uL) and 96% formic acid (0.83 uL, 0.022 mmol) and was stirred at room-temperature for 24 h. It was noted that during the NMA addition a precipitate started to crystallize out, and was analyzed and found to be the crude title compound (I2). Filtration gave a pale-yellow powder (14.5 mg, 41% crude yield) that was recrystallized from a minimum volume of absolute ethanol (˜0.75 mL) yielding 13 mg (37%) of the title compound as pale-yellow, microcrystalline flakes: mp 131.5-132° C.; HRMS calcd for C19H22N3O4 (M+H+) 356.1610, obsd 356.15571; 1H NMR (300 MHz, DMSO-d6) δ 3.737 (s, 6H), 4.621 (s, 4H), 6.891, 6.885, 6.869, 6.862 (dd, 4H), 7.196-7.167 (d, 4H), 8.840 (s, 2H), ˜11.7 (br s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 145.704, 135.410, 135.380, 128.787, 128.382, 128.199, 127.879, 127.230, 120.561, 64.383, 57.309, 52.166; Anal. Calcd for C19H21N3O4 (355.39): C, 64.21; H, 5.96; N, 11.82. Found: C, 64.04; H, 5.96; N, 11.86.

Workup

  1. additionIt was noted that during the NMA addition a precipitate
  2. customto crystallize out
  3. filtrationFiltration
  4. customgave a pale-yellow powder (14.5 mg, 41% crude yield) that
  5. customwas recrystallized from a minimum volume of absolute ethanol (˜0.75 mL)

Sources & evidence

ORD record
ord-6b1288db89144606ba20f1b32437865d
Source dataset
uspto-grants-2014_10
Patent number
US08853220B1

Reaction notes

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