4-(dimethylamino)-3-nitrobenzoic acid → HCID 67528395, compound

HRID 219945Notes

Reaction equation

HRID 219945 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1.[CH3:16][N:17]([CH3:30])[C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=O)=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]>CO>[CH3:30][N:17]([CH3:16])[C:18]1[CH:26]=[CH:25][C:21]([C:22]2[O:15][N:14]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=3)[N:1]=2)=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 36848044-(dimethylamino)-3-nitrobenzoic acidHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 67528395HCID 67528395, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was obtained following procedure described for example 4, step 1, but starting from Intermediate 1 (300 mg; 1.41 mmol) and Intermediate 35 (326.90 mg; 1.56 mmol). Title compound was isolated after trituration with MeOH as a brown powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.50 (d, J=2.1 Hz, 1H), 8.16 (dd, J=9.1, 2.2 Hz, 1H), 8.09 (d, J=7.2 Hz, 1H), 8.03 (dd, J=8.2, 1.5 Hz, 1H), 7.98-7.94 (m, 1H), 7.38 (d, J=9 Hz, 1H), 3.90 (s, 3H), 2.99 (s, 6H). LC/MS (Method B): 387.2 (M+H)+. HPLC (Method A) Rt. 5.07 min (purity: 98%).

Sources & evidence

ORD record
ord-9017b6f521dc4a0c965d9771e560999e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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