HCID 58902321, compound → HCID 58902426, compound

HRID 1640144Notes

Reaction equation

HRID 1640144 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:13]C(=O)OC(C)(C)C)[CH:8]=[C:9]([C:11]#[N:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>Cl.O1CCOCC1>[NH2:13][C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=1)[C:11]#[N:12]

Participants

4

Reactant 1

HCID 58902321HCID 58902321, compound

Product 1

HCID 58902426HCID 58902426, compoundYield 186.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (3-tert-butyl-5-cyanophenyl)carbamate (4.29 g, 0.0133 mol) in 4M HCl in dioxane (18 mL) was allowed to stir at rt for 2 h. The reaction mixture was concentrated to give 3-amino-5-tert-butylbenzonitrile (4.33 g, 93%) which was used without further purification. 1H NMR (300 MHz, CD3OD) δ: 7.99 (m, 1H), 7.72 (m, 1H), 7.56 (m, 1H), and 1.37(s, 9H). LCMS ES+ 175.1, ES− 173.1.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-74ba590aad6049cdb49fba120c615b44
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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