2,3-Dichloroaniline → HCID 11706040, compound

HRID 2067297Notes

Reaction equation

FC1C=C(F)C=CC=1NC1C=CC(C(C2C=C(N3C=C(CCO)N=N3)C=CC=2C)=O)=C(C)C=1.Br[C:35]1[CH:40]=[CH:39][C:38]([C:41]([C:43]2[CH:48]=[C:47]([N:49]3[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]3)[CH:46]=[CH:45][C:44]=2[CH3:57])=[O:42])=[C:37]([Cl:58])[CH:36]=1.[Cl:59][C:60]1[C:65]([Cl:66])=[CH:64][CH:63]=[CH:62][C:61]=1[NH2:67]>>[Cl:58][C:37]1[CH:36]=[C:35]([NH:67][C:61]2[CH:62]=[CH:63][CH:64]=[C:65]([Cl:66])[C:60]=2[Cl:59])[CH:40]=[CH:39][C:38]=1[C:41]([C:43]1[CH:48]=[C:47]([N:49]2[CH:53]=[C:52]([CH2:54][CH2:55][OH:56])[N:51]=[N:50]2)[CH:46]=[CH:45][C:44]=1[CH3:57])=[O:42]

Participants

Reactant 3

HCID 118442,3-Dichloroaniline

HCID 11510648HCID 11510648, compound

HCID 69606498HCID 69606498, compound

Product 1

HCID 11706040HCID 11706040, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 148, using compound 471 (0.13 mmol) and 2,3-dichloro-phenylamine (0.13 mmol). The crude product was purified by flash chromatography using MeOH/DCM 1:20 as the eluent to afford the title compound. 13C NMR (CDCl3) δ 194.9, 146.4, 140.4, 139.1, 138.5, 135.1, 134.8, 134.0, 133.5, 132.7, 130.0, 127.6, 124.3, 123.2, 122.5, 121.0, 119.9, 118.6, 117.4, 115.2, 61.5, 28.7, 20.1

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-a5dcbcf763b84cb1a641bcdd8e2b4a2e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293772B2

Reaction notes

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