2-Naphthylamine → 1-Chloro-naphthalen-2-ylamine

HRID 1864608

Reaction equation

HRID 1864608 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11].C1C(=O)N([Cl:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:19][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11]

Participants

4

Reactant 2

HCID 70572-NaphthylamineHCID 31398Chlorosuccinimide

Product 1

HCID 4180141-Chloro-naphthalen-2-ylamineYield 96.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
49 °C

Procedure

To a CCl4 (600 mL) solution of 2-naphthylamine (10 g) at 49° C. was added NCS (9.51 g, 1.02 eq) in portions. The mixture was stirred at 49° C. for 1.5 h then concentrated to dryness to give 1-chloro-2-naphthylamine (11.94 g, 96%) as a dark solid. MS Found: (M+H)+=178.

Workup

  1. concentrationthen concentrated to dryness

Sources & evidence

ORD record
ord-b3aa8510d4024a85bb81e219ef6b4778
Source dataset
uspto-grants-2009_12
Patent number
US07625921B2

Linked notes

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