Sodium Azide → HCID 36419, compound

HRID 2116098Notes

Reaction equation

HRID 2116098 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(OC)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:28]([CH2:31][CH:32]1[CH2:36][C:35]2[CH:37]=[CH:38][CH:39]=[C:40]([O:41][CH3:42])[C:34]=2[O:33]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[CH3:42][O:41][C:40]1[C:34]2[O:33][CH:32]([CH2:31][NH2:28])[CH2:36][C:35]=2[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 19886353HCID 19886353, compoundHCID 86599172HCID 86599172, compound

Product 1

HCID 36419HCID 36419, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.00 g, 2.99 mmol) with sodium azide (0.78 g, 11.96 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-methoxy-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.06 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.465 g (54%) (±)-1-(7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 168-171° C.; Anal. calcd. for C10H13NO2HCl: C, 55.69; H, 6.54; N, 6.49. Found: C, 55.68; H, 6.52; N, 6.5.

Sources & evidence

ORD record
ord-083c4a983bcb4ed5b2661ed62dec876b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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