3-(Dimethylamino)-1-propanol → 6-Chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one Hydrochloric acid salt

HRID 495132Notes

Reaction equation

HRID 495132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[OH:13].[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18]O>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][C:7](=[O:12])[CH:6]=[C:5]([O:13][CH2:18][CH2:17][CH2:16][N:15]([CH3:20])[CH3:14])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 766463-(Dimethylamino)-1-propanolHCID 546863486-Chloro-4-hydroxycoumarin

Product 1

HCID 865969226-Chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one Hydrochloric acid saltYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Is prepared via method B from 6-chloro-4-hydroxycoumarin and 3-dimethylamino-propan-1-ol using 4M HCl in dioxane to form the title compound as the hydrochloric acid salt (332 mg, 73%). 1H NMR (DMSO-d6, 300 MHz) δ 10.23 (1H, s), 7.88 (1H, d, J=2.75 Hz), 7.73 (1H, dd, J=2.75, 9 Hz), 7.48 (1H, d, J=9Hz), 6.0 (1H, s), 4.31 (2H, t, J=5.75 Hz), 3.28 (2H, m), 2.80 (3H, s), 2.80 (3H, s), 2.24 (2H, m); MS (ESI, Pos.) calcd for C14H16ClNO3 m/z [M+H]=282.1, found 282.1.

Sources & evidence

ORD record
ord-23db4ebfa4f74ba9a31d1e6a78bae0c7
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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