Sodium Nitrite → HCID 67956040, compound

HRID 872273Notes

Reaction equation

HRID 872273 reaction equation
N([O-])=[O:2].[Na+].[CH:5]1([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17](N)=[CH:18][C:13]=3[N:12]=[N:11]2)[CH2:8][CH2:7][CH2:6]1>S(=O)(=O)(O)O>[CH:5]1([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:2])=[CH:18][C:13]=3[N:12]=[N:11]2)[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 67956512HCID 67956512, compound

Product 1

HCID 67956040HCID 67956040, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite (61 mg, 0.89 mmol, 1.2 equiv) was added to a solution of 1-(cyclobutylmethyl)-1H-benzotriazol-5-amine (3-3, 150 mg, 0.74 mmol, 1 equiv) in 20% aqueous sulfuric acid solution (5 mL) and the resulting mixture was irradiated at 120° C. in a microwave reactor for 40 min. The reaction mixture was cooled to ambient temperature and then partitioned between water (300 mL) and ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (hexanes, grading to 100% ethyl acetate) to give 1-(cyclobutylmethyl)-1H-benzotriazol-5-ol (3-4) as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.45 (d, 1H, J=2.1 Hz), 7.42 (d, 1H, J=8.9 Hz), 7.16 (dd, 1H, J=8.9, 2.1 Hz), 6.39 (br s, 1H), 4.61 (d, 2H, J=7.3 Hz), 2.99 (p, 1H, J=7.6 Hz), 2.08 (m, 2H), 1.91 (m, 4H) ppm. LRMS m/z (M+H) 204.0 found, 204.1 required.

Workup

  1. customthe resulting mixture was irradiated at 120° C. in a microwave reactor for 40 min
  2. custompartitioned between water (300 mL) and ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (hexanes, grading to 100% ethyl acetate)

Sources & evidence

ORD record
ord-46983731e0c44d8bacbcfa52c83b087c
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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