Sodium Azide → (+/-)-1-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine

HRID 2116172Notes

Reaction equation

HRID 2116172 reaction equation
CC1C=CC(S(OCC2CC3C=C(Cl)C=C(OC)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:29]([CH2:32][CH:33]1[CH2:37][C:36]2[CH:38]=[C:39]([Cl:44])[CH:40]=[C:41]([O:42][CH3:43])[C:35]=2[O:34]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pt]>[Cl:44][C:39]1[CH:40]=[C:41]([O:42][CH3:43])[C:35]2[O:34][CH:33]([CH2:32][NH2:29])[CH2:37][C:36]=2[CH:38]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86598566(+/-)-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599229(+/-)-2-(Azidomethyl)-5-chloro-7-methoxy-2,3-dihydro-1-benzofuran

Product 1

HCID 68961804(+/-)-1-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamineYield 56%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Treatment of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.10 g, 2.98 mmol) with sodium azide (1.5 g, 23.1 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-chloro-7-methoxy-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.080 g, 5 wt. %) generally according to the procedure described for Example 1 afforded 0.415 g (56%) of (±)-1-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 195-198° C.; Anal. calcd. for C10H12ClNO2HCl: C, 48.02; H, 5.24; N, 5.6. Found: C, 46.41; H, 5.09; N, 5.31.

Sources & evidence

ORD record
ord-918f5e37e4444b7b8b37207b3e91ab11
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…