1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → 2-(2-Isobutoxy-4-(dimethylamino)benzoyl)benzoic acid

HRID 839546Notes

Reaction equation

HRID 839546 reaction equation
CN(C)[C:3]1[CH:4]=[C:5]2[C:10](=[O:11])[O:9][C:7](=[O:8])[C:6]2=[CH:12][CH:13]=1.CN(C)[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:25])[CH3:24])[CH:18]=1>[Cl-].[Zn+2].[Cl-].ClC1C=CC=CC=1>[CH2:7]([O:8][C:17]1[CH:18]=[C:19]([N:23]([CH3:25])[CH3:24])[CH:20]=[CH:21][C:22]=1[C:10]([C:5]1[CH:4]=[CH:3][CH:13]=[CH:12][C:6]=1[C:7]([OH:9])=[O:8])=[O:11])[CH:6]([CH3:12])[CH3:5]

Participants

5

Reactant 2

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-HCID 114354424-(Dimethylamino)phthalic anhydride

Product 1

HCID 233433772-(2-Isobutoxy-4-(dimethylamino)benzoyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

In a manner similar to that of part A of Example 3 condensation of 4-(dimethylamino)phthalic anhydride (1.91 g.) and N,N,N',N'-tetramethyl-m-phenylenediamine (1.64 g.) in contact with zinc chloride (2.70 g.) and with chlorobenzene (50 ml.) as diluent afforded 2-(2,4-bis(dimethylamino)benzoyl)-4-(dimethylamino)benzoic acid (II: Y'2 = Y'4 = Z'5 = (CH3)2N, Z4 = Z'6 = Z7 = H) (m.p. 216°-222° C.) or the 5-(dimethylamino) isomer thereof.

Sources & evidence

ORD record
ord-01848f2379704d15936fd248cef5cd2d
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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