HCID 67956270, compound → HCID 67956512, compound

HRID 872272Notes

Reaction equation

HRID 872272 reaction equation
[CH:1]1([CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:9]=3[N:8]=[N:7]2)[CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][C:13]([NH2:15])=[CH:14][C:9]=3[N:8]=[N:7]2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 67956270HCID 67956270, compound

Product 1

HCID 67956512HCID 67956512, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 1-(cyclobutylmethyl)-5-nitro-1H-benzotriazole (3-2, 1.2 g, 5.17 mmol, 1 equiv) and 10% palladium on carbon (0.6 g) in ethanol (50 mL) was stirred at 23° C. under a hydrogen balloon for 20 h. The catalyst was filtered onto a pad of diatomaceous earth and washed with ethanol (100 mL). The filtrate was concentrated to give 1-(cyclobutylmethyl)-1H-benzotriazol-5-amine (3-3) as a grey solid. 1H NMR (300 MHz, CDCl3) δ 7.32 (d, 1H, J=8.9 Hz), 7.20 (d, 1H, J=1.8 Hz), 6.92 (dd, 1H, J=8.5, 1.8 Hz), 4.56 (d, 2H, J=7.3 Hz), 3.80 (br s, 2H), 2.95 (p, 1H, J=7.3 Hz), 2.05 (m, 2H), 1.88 (m, 4H) ppm. LRMS m/z (M+H) 203.0 found, 203.1 required.

Workup

  1. filtrationThe catalyst was filtered onto a pad of diatomaceous earth
  2. washwashed with ethanol (100 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0d5c18aaa1f346b8ad5f02548cd62d34
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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