Chloroform → N-Phenyl-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 918236Notes

Reaction equation

[C:1]1([NH:7][CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(NN)(C1C=CC(C)=CC=1)(=O)=O.C(Cl)(Cl)Cl>C(O)C>[C:1]1([NH:7][CH:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -10 °C

Procedure

2.37 grams (0.01 mol.) of 2-phenylaminotetralone (formula I: R = phenyl) are refluxed during 6 hours in 50 ml of ethanol, in the presence of one equivalent of tosylhydrazine. After the removal of the alcohol, 100 ml of alcohol-free chloroform are added to the residue (crude tosylhydrazone). After cooling to -10°C, 0.011 mol. of catecholborane are added and the reaction is allowed to take place during 30 minutes. 0.03 mol. of trihydrated sodium acetate are then added so as to initiate the decompositon of the intermediate addition product and the mixture is refluxed during 1 hour. After cooling, 100 ml of water are added and the pH is adjusted at 13. The obtained 2-phenylaminotetraline (yield: 80%) is extracted by means of chloroform and converted into hydrochloride. Melting point: 193° - 196°C.

Workup

customAfter the removal of the alcohol, 100 ml of alcohol-free chloroform
additionare added to the residue (crude tosylhydrazone)
additionof catecholborane are added
customduring 30 minutes
additionof trihydrated sodium acetate are then added so as
additionthe decompositon of the intermediate addition product
temperaturethe mixture is refluxed during 1 hour
temperatureAfter cooling
addition100 ml of water are added

Sources & evidence

ORD record: ord-9f0ba472386147b1bfa29cbd27810486
Source dataset: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03970650

Reaction notes

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