HCID 86666126, compound → HCID 67774679, compound

HRID 2040720Notes

Reaction equation

HRID 2040720 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:15])([CH3:14])[CH2:11][O:12][CH3:13])=[CH:6][C:5]=1[N+:16]([O-])=O)=[N+]=[N-]>CCO.[Pd]>[CH3:13][O:12][CH2:11][C:10]([C:7]1[CH:6]=[C:5]([NH2:16])[C:4]([NH2:1])=[CH:9][CH:8]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 1

HCID 86666126HCID 86666126, compound

Product 1

HCID 67774679HCID 67774679, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Azido-4-(1-methoxy-2-methylpropan-2-yl)-2-nitrobenzene (1.102 g, 3.52 mmol) was dissolved in EtOH (30 ml) and Pd/C (10% wt.) (0.110 g, 10% wt) was added. The reaction was purged 3 times with N2 then 3 times with H2 and the reaction stirred at r.t. overnight. The mixture was filtered through Celite and the filtrate was concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% heptane to 100% EtOAc as eluent to give the product as a pale brown oil which solidified into a dark orange solid (0.481 g, 63%, 90% pure): MS (ESI+) for C11H18N2O m/z 195.1 [M+H]+; LC purity 87% (ret. time, 0.99 min); 1H NMR (500 MHz, CDCl3) δH 16.65 (dd, J=11.2, 1.9 Hz, 2H), 6.58 (d, J=7.9 Hz, 1H), 3.26 (s, 2H), 3.24 (s, 3H), 1.20 (s, 6H).

Workup

  1. customThe reaction was purged 3 times with N2
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give the crude product
  5. customThe product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-75f6efbf9a76459b8711430d89a1850e
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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