Sulfuric Acid → HCID 89586637, compound

HRID 530970Notes

Reaction equation

HRID 530970 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:3]=1[C:19]#[N:20].S(=O)(=O)(O)[OH:22].[OH-].[Na+]>>[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:3]=1[C:19]([NH2:20])=[O:22]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 895865895-amino-1-isopropyl-3-(3-nitrophenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 89586637HCID 89586637, compoundYield 85%

Conditions

Temperature
65 °C

Procedure

Compound 26 (100 mg, 0.369 mmol) was added to concentrated sulfuric acid (1 mL) and heated to 65° C. for 3 hours. Afterwards, the reaction mixture was poured into ice water and the pH was brought to 14 with 10 M NaOH. The aqueous material was extracted several times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to a solid (91 mg, 85% yield): 1H NMR (400 MHz, DMSO) δ 8.32 (s, 1H), 8.21 (d, J=8.2, 1H), 7.98 (d, J=7.7, 1H), 7.69 (t, J=8.0, 1H), 6.20 (br, 2H), 4.51 (hept, 1H), 1.35 (d, J=6.5, 6H); 13C NMR (100 MHz, DMSO) δ 166.17, 149.37, 147.65, 145.50, 135.63, 134.92, 129.69, 122.79, 122.43, 95.43, 47.11, 21.50; [M+H]+ calculated for C13H15N5O3 290.1, found 290.0.

Workup

  1. extractionThe aqueous material was extracted several times with dichloromethane
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-74cc9de204c14692bee82c0de5a1f8a8
Source dataset
uspto-grants-2016_05
Patent number
US09353116B2

Reaction notes

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