Hydrazine → HCID 58490205, compound

HRID 1395867Notes

Reaction equation

HRID 1395867 reaction equation
Cl.[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[NH:14])OCC)=[CH:6][CH:5]=1.C(O)(=O)C.[CH:19]([NH2:21])=[NH:20].NN.[N:24]([O-])=O.[Na+]>O.C(O)(=O)C>[N:20]1[CH:19]=[N:21][N:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)[N:24]=1

Participants

7

Reactant 4

HCID 9321HydrazineHCID 160693Formamidine acetateHCID 23668193Sodium NitriteHCID 131732102HCID 131732102, compound

Product 1

HCID 58490205HCID 58490205, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(hydroxymethyl)-benzenecarboximidic acid, ethyl ester, hydrochloride (1 mmol, 216 mg) and formamidine acetate (5 mmol, 521 mg) was added anhydrous hydrazine (20 mmol, 630 uL) the resulting viscous oil was allowed to stir. After 1 hour, acetic acid (3 mL) was added followed by sodium nitrite (690 mg, 10 mmol) as a finely divided powder. The now bright pink solution was allowed to stir for 15 minutes and then diluted with 15 mL of water. The aqueous crude reaction was subsequently extracted with methylene chloride (4×10 mL). The organic extracts were dried with MgSO4. After solvent removal, the crude pink product was purified by flash chromatography (silica gel) first washing with 100% methylene chloride, followed by methylene chloride with 1% methanol, giving (4-(1,2,4,5-tetrazin-3-yl)phenyl)methanol (40 mg, 21%) as a bright pink solid. LRMS-ESI [M+H]− calcd. for C9H9N4O−: 189.08, found: 188.8.

Workup

  1. stirringto stir for 15 minutes
  2. customThe aqueous crude reaction
  3. extractionwas subsequently extracted with methylene chloride (4×10 mL)
  4. dry with materialThe organic extracts were dried with MgSO4
  5. customAfter solvent removal
  6. customthe crude pink product was purified by flash chromatography (silica gel)
  7. washfirst washing with 100% methylene chloride

Sources & evidence

ORD record
ord-92064e337d62481ba3bdbac56edfb73e
Source dataset
uspto-grants-2014_12
Patent number
US08900549B2

Reaction notes

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