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Cesium carbonate → 3-(3-Ethoxy-4-methoxyphenylamino)phthalic acid dimethyl ester

HRID 448337
Notes
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Reaction equation

HRID 448337 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10](I)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[NH2:22])[CH3:17].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH:22][C:21]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:19]([O:18][CH2:16][CH3:17])[CH:20]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalateHCID 167919473-Ethoxy-4-methoxyaniline

Product 1

HCID 583072013-(3-Ethoxy-4-methoxyphenylamino)phthalic acid dimethyl esterYield 80%

Reagents, catalysts & solvents 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 3-ethoxy-4-methoxyaniline (0.51 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.90 g of the product at 70:30 hexanes-ethyl acetate, in 80% yield: 1H NMR (CDCl3) δ 1.45 (t, J=7.0 Hz, 1H), 3.86 (s, 3H), 3.87 (s, 3H), 3.88 (s, 3H), 4.05 (q, J=7.0 Hz, 2H), 6.71-6.74 (m, 2H), 6.84 (d, J=7.4 Hz, 1H), 6.96 (dd, J=7.3 Hz, J=1.0 Hz, 1H), 7.13 (dd, J=8.5 Hz, J=1.0 Hz, 1H), 7.24 (t, J=7.4 Hz, 1H), 8.07 (s, 1H).

Workup

  1. temperatureto reflux under nitrogen for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. washthe filter was washed with additional CH2Cl2 (30 mL)
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed
  7. washeluting 0.90 g of the product at 70:30 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-f7a6019c949144e88b8b615a09112457
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481568B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes