3-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one → 3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid isopropyl ester

HRID 1687803Notes

Reaction equation

HRID 1687803 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][C:6]1=[O:17]>C(O)(C)C>[CH:8]([O:7][C:6]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][CH2:2][CH2:3][CH2:4]1)=[O:17])([CH3:13])[CH3:9]

Participants

3

Reactant 1

HCID 672636543-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one

Product 1

HCID 672642723-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid isopropyl ester was prepared from 3-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one and isopropyl alcohol in an analogous manner to Example 1426a. Product isolated as a yellow oil (413 mg, 63%). LCMS (m/e) 281 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.89-7.81 (m, 2H), 7.55-7.35 (m, 1H), 5.10-4.96 (m, 1H), 4.24 (t, 2H, J=5.5 Hz), 3.85 (t, 2H, J=5.6 Hz), 2.20-2.09 (m, 2H), 1.27 (d, 6H, J=5.7 Hz).

Sources & evidence

ORD record
ord-0b815f4d05a3448fa3e366af2db421e2
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…