Acetic Acid → 3-[(Furan-2-yl-methyl)-amino]-phthalic acid dimethyl ester

HRID 1160264Notes

Reaction equation

HRID 1160264 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH:14][CH2:21][C:17]2[O:16][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7362FurfuralHCID 5049666Sodium triacetoxyborohydrideHCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylate

Product 1

HCID 597545943-[(Furan-2-yl-methyl)-amino]-phthalic acid dimethyl esterYield 109.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-amino-phthalic acid dimethyl ester (8.23 g, 39.32 mmol) in methylene chloride (200 ml) under a nitrogen atmosphere, 2-furaldehyde (8.14 ml, 98.30 mmol) and acetic acid (13.57 ml, 235.92 mmol) were added. The mixture was stirred for 5 minutes, followed by addition of sodium triacetoxyborohydride (25 g, 117.96 mmol). The reaction was stirred overnight, washed with water (2×200 ml), saturated aqueous sodium bicarbonate (2×200 ml), and brine (200 ml), and dried over MgSO4. The solvent was evaporated in vacuo to give a brown oil (12.42 g), which was used directly without purification.

Workup

  1. stirringThe reaction was stirred overnight
  2. washwashed with water (2×200 ml), saturated aqueous sodium bicarbonate (2×200 ml), and brine (200 ml)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-433a22374b294534ba155ad7c4677e34
Source dataset
uspto-grants-2010_10
Patent number
US07816393B2

Reaction notes

Loading…