Hydrochloric Acid → HCID 67299086, compound

HRID 2283139Notes

Reaction equation

HRID 2283139 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][NH:13][N:14]=2)[CH:7]=[CH:6][C:5]=1[NH2:15])([O-])=O.[ClH:16]>CO.[Pd]>[ClH:16].[ClH:16].[N:14]1[NH:13][N:12]=[N:11][C:10]=1[C:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13216719HCID 13216719, compound

Product 1

HCID 67299086HCID 67299086, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-Nitro-4-(2H-tetrazol-5-yl)-phenylamine (6.80 g) in methanol (450 ml) and 40% (v/v) hydrochloric acid (20 ml) was added 10% Pd on carbon. The reaction vessel was evacuated and charged with hydrogen using a balloon. After 4 hours the reaction was analyzed by HPLC. Water was added (100 ml) and the reaction mixture filtered. The catalyst was washed with 50% v/v methanol in water (100 ml). The solvents were evaporated under reduced pressure (175 mBar then 50 mBar) at 40° C. to yield a brownish colored solid 4-(2H-tetrazol-5-yl)-benzene-1,2-diamine dihydrochloride (6.45 g), Rt=4.9 mins. 1H NMR (d6-DMSO, 400 MHz) 7.82 ppm (1H d, 2 Hz), 7.67 ppm (1H, d of d, 8.5 Hz, 2 Hz), 7.03 ppm (1H, d, 8.4 Hz), MS: (Electrospray+) 176.8 m/z (M+), 198.7 m/z (M+Na).

Workup

  1. customThe reaction vessel was evacuated
  2. additioncharged with hydrogen using a balloon
  3. additionWater was added (100 ml)
  4. filtrationthe reaction mixture filtered
  5. washThe catalyst was washed with 50% v/v methanol in water (100 ml)
  6. customThe solvents were evaporated under reduced pressure (175 mBar

Sources & evidence

ORD record
ord-919599f74991409db13a525985b6c308
Source dataset
uspto-grants-2015_09
Patent number
US09144757B2

Reaction notes

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