3-Nitrobenzaldehyde → HCID 178526625, compound

HRID 1490101Notes

Reaction equation

HRID 1490101 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].O.[NH2:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1>C(O)C.C(O)(=O)C>[NH:15]1[C:14]([NH:13][CH2:7][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[CH:10][CH:9]=2)=[N:18][N:17]=[N:16]1

Participants

5

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 178509300HCID 178509300, compound

Product 1

HCID 178526625HCID 178526625, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 3-nitrobenzaldehyde (1.51 g) and 5-aminotetrazole monohydrate (1.03 g)in absolute ethanol (30 ml) and glacial acetic acid (0.57 ml) was stirred at room temperature for 40 minutes and then refluxed under nitrogen for 5 hours 30 minutes. Solvents were removed under high vacuum and the remaining solid was suspended in absolute ethanol (50 ml) and treated at room temperature with solid sodium borohydride (1.2 g) over 20 minutes. After a further 15 hours of stirring, the solvent was removed under vacuum and the residue was dissolved in water (100 ml) and extracted with diethyl ether (2×30 ml). The basic aqueous phase was acidified to pH 2 with 2N hydrochloric acid and the precipitated solid was collected by filtration, washed with water, diethyl ether, and finally recrystallized from absolute ethanol to give the title compound (420 mg) as white needles; mp 208°-210° C.; δH (250 MHz, DMSO-d6) 8.21 (1H, br s, Ar--H), 8.12 (1H, br d, J=9 Hz, Ar--H), 7.80 (1H, d, J=8 Hz, Ar--H), 7.70 (1H, br t, J=6.3 Hz, --NH--), 7.64 (1H, t, J=8 Hz, Ar--H), 4.53 (2H, d, J=6.3 Hz, --CH2 --); m/z (CI) 220 (M-).

Workup

  1. temperaturerefluxed under nitrogen for 5 hours 30 minutes
  2. customSolvents were removed under high vacuum
  3. additiontreated at room temperature with solid sodium borohydride (1.2 g) over 20 minutes
  4. stirringAfter a further 15 hours of stirring
  5. customthe solvent was removed under vacuum
  6. dissolutionthe residue was dissolved in water (100 ml)
  7. extractionextracted with diethyl ether (2×30 ml)
  8. filtrationthe precipitated solid was collected by filtration
  9. washwashed with water, diethyl ether
  10. customfinally recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-63602420c09e4912ab2d34390d5e2d33
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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