(+/-)-2-(Azidomethyl)-2,3-dihydronaphtho[1,2-b]furan → (+/-)-1-(2,3-Dihydronaphtho[1,2-b]furan-2-yl)methanamine

HRID 13963Notes

Reaction equation

HRID 13963 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8]2[C:10]3[C:15]([CH:16]=[CH:17][C:7]=2[CH2:6]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N+]=[N-]>[Pd]>[O:9]1[CH:5]([CH2:4][NH2:1])[CH2:6][C:7]2[CH:17]=[CH:16][C:15]3[C:10]([C:8]1=2)=[CH:11][CH:12]=[CH:13][CH:14]=3

Participants

3

Reactant 1

HCID 86047400(+/-)-2-(Azidomethyl)-2,3-dihydronaphtho[1,2-b]furan

Product 1

HCID 11390012(+/-)-1-(2,3-Dihydronaphtho[1,2-b]furan-2-yl)methanamineYield 103.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-2-(azidomethyl)-2,3-dihydronaphtho[1,2-b]furan (1.61 g, 7.15 mmol) with palladium on carbon (10 wt. %, 0.160 g) generally according to the procedure described for Example 2 afforded 1.48 g (88%) of (±)-1-(2,3-dihydronaphtho[1,2-b]furan-2-yl)methanamine as a white solid, hydrochloride salt. mp>250° C. (dec.); Anal. calcd. for C13H13NOHCl: C, 66.24; H, 5.99; N, 5.94. Found: C, 66.23; H, 6.07; N, 5.77.

Sources & evidence

ORD record
ord-34c086fef076480dab61ee7a74e278e3
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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