O-Xylene → HCID 19802911, compound

HRID 1645929Notes

Reaction equation

HRID 1645929 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15]C)[CH2:6]1)[CH2:2][CH3:3].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1CC(O)=O.B(Br)(Br)Br.[C:35]1(C)C(C)=CC=C[CH:40]=1>>[CH2:1]([N:4]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[CH2:6]1)[CH2:35][CH2:40][C:25]1[C:26]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][CH:24]=1)[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 7237O-XyleneHCID 113932-Naphthaleneacetic acidHCID 25134Boron tribromideHCID 102425482-Propylamino-5-methoxytetralin

Product 1

HCID 19802911HCID 19802911, compound

Procedure

A mixture of 2-(N-n-propylamino)-5-methoxytetralin, 2-naphthylacetic acid and trimethylaminoborohydride in dry xylene was refluxed under an atmosphere of nitrogen as described by Horn et al. Pharm. Weekbld. Sci. Ed. 7 208-211, 1985. The resulting methoxy intermediate was demethylated using boron tribromide as described in the above article to yield the desired product.

Workup

  1. temperaturewas refluxed under an atmosphere of nitrogen

Sources & evidence

ORD record
ord-929376223acf47478e197a572afb5ac0
Source dataset
uspto-grants-1993_01
Patent number
US05177112

Reaction notes

Loading…