5-(Hydroxymethyl)furfural → 3-[(5-Hydroxymethyl-furan-2-ylmethyl)-amino]-phthalic acid dimethyl ester

HRID 906789

Reaction equation

HRID 906789 reaction equation
O[CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12](=[O:29])[C:13]1[C:14](=[C:19]([NH:23]CCCCC)[CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH3:18])=[O:16]>>[CH3:10][O:11][C:12](=[O:29])[C:13]1[C:14](=[C:19]([NH:23][CH2:2][C:3]2[O:7][C:6]([CH2:8][OH:9])=[CH:5][CH:4]=2)[CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 2373325-(Hydroxymethyl)furfuralHCID 210401313-Pentylamino-phthalic acid dimethyl ester

Product 1

HCID 210401373-[(5-Hydroxymethyl-furan-2-ylmethyl)-amino]-phthalic acid dimethyl esterYield 76%

Procedure

5-Hydroxymethyl-furan-2-carbaldehyde (0.95 ml, 7.5 mmol) was treated in the same manner as described above for the synthesis of 3-pentylamino-phthalic acid dimethyl ester. The residue (oil) was purified by chromatography (SiO2, 40/60 ethyl acetate/hexanes) to give 0.97 g (76%) of yellow oil: 1H NMR (CDCl3) δ 7.35-7.27 (m, 1H), 7.05 (bs, 1H), 6.87-6.83 (m, 2H), 6.21 (d, J=3.1 Hz, 1H), 6.17 (d, J=3.2 Hz, 1H), 4-57 (s, 2H), 4.38 (bs, 2H) 3.86 (s, 3H), 3.83 (s, 3H), 1.98 (bs, 1H).

Workup

  1. customThe residue (oil) was purified by chromatography (SiO2, 40/60 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dc953ab247024958aa9058f23180558b
Source dataset
uspto-grants-2011_09
Patent number
US08012997B2

Linked notes

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