Potassium → 3-[2,4-Bis(dimethylamino)phenyl]-3-(4-diethylaminophenyl)-6-dimethylaminophthalide

HRID 569675Notes

Reaction equation

[K].[CH3:2][N:3]([CH3:37])[C:4]1[CH:33]=[C:32]([N:34]([CH3:36])[CH3:35])[CH:31]=[CH:30][C:5]=1[CH:6]([C:18]1[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:8]=1>>[CH3:37][N:3]([CH3:2])[C:4]1[CH:33]=[C:32]([N:34]([CH3:35])[CH3:36])[CH:31]=[CH:30][C:5]=1[C:6]1([C:7]2[CH:8]=[CH:9][C:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:11][CH:12]=2)[C:18]2[C:19](=[CH:23][C:24]([N:27]([CH3:28])[CH3:29])=[CH:25][CH:26]=2)[C:20](=[O:22])[O:21]1

Participants

Reactant 2

HCID 5462222Potassium

HCID 201478142-[2,4-Bis(dimethylamino)-4'-diethylaminobenzhydryl]-5-dimethylaminobenzoic acid

Product 1

HCID 156069463-[2,4-Bis(dimethylamino)phenyl]-3-(4-diethylaminophenyl)-6-dimethylaminophthalide

Procedure

Employing a procedure similar to that described in Example 1, part C above, the potassium salt of 2-[2,4-bis(dimethylamino)-4'-diethylaminobenzhydryl]-5-dimethylaminobenzoic acid from A was oxidized to obtain 11.4 g of 3-[2,4-bis(dimethylamino)phenyl]-3-(4-diethylaminophenyl)-6-dimethylaminophthalide (Formula I: R=CH3 ; X=H; Y=4-(C2H5)2NC6H4 ; Z=2,4-[(CH3)2N]2C6H3) as a tan solid melting at 123°-125° C.

Sources & evidence

ORD record: ord-4183156d03fa4837997620d7081ac4cc
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732991

Reaction notes

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