Hydrazine → 4-Amino-2-(4-amino-2-hydroxybutoxy)benzonitrile

HRID 474286Notes

Reaction equation

HRID 474286 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH:14]([OH:28])[CH2:15][O:16][C:17]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:18]=1[C:19]#[N:20].NN>CCO>[NH2:25][C:23]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([O:16][CH2:15][CH:14]([OH:28])[CH2:13][CH2:12][NH2:3])[CH:24]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 666683592-(4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutoxy)-4-nitrobenzonitrile

Product 1

HCID 666661314-Amino-2-(4-amino-2-hydroxybutoxy)benzonitrileYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-(4-(1,3-dioxoisoindolin-2-yl)-2-hydroxybutoxy)-4-nitrobenzonitrile (2.96 g, 7.76 mmol) in EtOH (28.1 mL) was added hydrazine (12.18 mL, 388 mmol). The reaction mixture was heated at 50° C. for 1.5 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated and taken up in CH2Cl2. The solid was filtered off again, and the filtrate was concentrated and purified by Prep-HPLC to obtain 4-amino-2-(4-amino-2-hydroxybutoxy)benzonitrile (1.015 g, 59.1% yield). LC-MS (M+H)+=222.1. 1H NMR (500 MHz, methanol-d4) δ 7.24 (d, J=8.5 Hz, 1H), 6.35-6.26 (m, 2H), 4.17-4.09 (m, 1H), 4.05 (dd, J=9.5, 4.9 Hz, 1H), 3.97 (dd, J=9.5, 5.5 Hz, 1H), 3.20 (t, J=7.0 Hz, 2H), 2.08 (td, J=7.1, 3.5 Hz, 1H), 2.01-1.86 (m, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. filtrationThe solid was filtered off again
  5. concentrationthe filtrate was concentrated
  6. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-78c83bdb3dcb4d99acd8edbf5b1be4f7
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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