Dimethylformamide → 4-(Diphenylamino)naphthalene-1-carbaldehyde

HRID 1608712Notes

Reaction equation

O=P(Cl)(Cl)Cl.C1(N(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]1([N:31]([C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN([CH:51]=[O:52])C>>[CH:51]([C:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]([N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:39][CH:40]=1)=[O:52]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11775Triphenylamine

HCID 24813Phosphorus oxychloride

HCID 11392281N,N-diphenyl-1-naphthylamine

Product 1

HCID 200871614-(Diphenylamino)naphthalene-1-carbaldehydeYield 40%

Procedure

The method of Example 4, Stage 1, was followed except that there was used 4.7 g of POCl3, 13.6 g of DMF, and in place of triphenylamine there was used N,N-diphenyl-1-naphthylamine (MW 295, 0.031M, 9.2 g) to give 4 g (40% yield) of 1-formyl-4-(N,N-diphenylamino) naphthalene as a yellow solid, m.p. 107°-110° C.

Sources & evidence

ORD record: ord-c66ab65158ab46908a6f87c31b7cc7d0
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05395969

Reaction notes

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