Ethyl Acetate → 6-Amino-7-benzyloxy-3-methoxychromen-2-one

HRID 643950Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([O:20][CH3:21])[C:15](=[O:19])[O:16]2)=[CH:11][C:10]=1[N+:22]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].CCOC(C)=O>C1COCC1.O>[NH2:22][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:16][C:15](=[O:19])[C:14]([O:20][CH3:21])=[CH:13]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 7-benzyloxy-3-methoxy-6-nitrochromen-2-one (0.20 g, 0.61 mmol) in 20 mL of THF is added a solution of Na2S2O4 (1.0 g) in water (6 mL). The mixture is heated at 80° C. for 18 h. Additional Na2S2O4 is added until the reaction is complete. After cooling to ambient temperature, EtOAc is added and the mixture is washed with water and sat. NaCl, then dried over sodium sulfate. The solvent is removed under reduced pressure to afford 6-amino-7-benzyloxy-3-methoxychromen-2-one as a pale yellow solid: 1H NMR (CDCl3) δ 7.44-7.34 (m, 5H), 6.81 (s, 1H), 6.70 (s, 1H), 6.68 (s, 1H), 5.11 (s, 2H), 3.85 (s, 3H); (M+H)+=298.

Workup

temperatureAfter cooling to ambient temperature
washthe mixture is washed with water and sat. NaCl
dry with materialdried over sodium sulfate
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-49a67cecf7304812b3055c42a4a534e0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700633B2

Reaction notes

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