Acetic Acid → o-Aminoacetanilide

HRID 2361932Notes

Reaction equation

HRID 2361932 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:30](O)(=[O:32])[CH3:31]>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:30](=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11149o-AminoacetanilideYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

N-(2-aminophenyl)acetamide (59 mg, 57%) as a yellow solid was synthesized from 1,2-diaminobenzene (216 mg, 2.00 mmol), EDCI (764 mg, 4.00 mmol), HOBt (540 mg, 4.00 mmol), DMAP (488 mg, 4.00 mmol), acetic acid (120 mg, 2.00 mmol) and DMF (1 mL) using the procedure similar to that described for compound 1 (Example 1): LCMS: 531 [M+1]+. 1H-NMR (400 MHz. DMSO-d6) δ 2.03 (s, 3H), 4.85 (s, 2H), 6.52 (m, 1H), 6.70 (m, 1H), 6.89 (m, 1H), 7.15 (m, 1H), 9.11 (s, 1H).

Sources & evidence

ORD record
ord-0b6beba9e6434f8799937b73a52b2498
Source dataset
uspto-grants-2014_04
Patent number
US08691820B2

Reaction notes

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