Water → HCID 25139342, compound

HRID 1669121Notes

Reaction equation

C([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([N+:20]([O-:22])=[O:21])=[C:12]([NH:16]C(=O)C)[CH:13]=2)[CH2:8]1)(=O)C.O.[CH]Cl>CO>[NH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[N+:20]([O-:22])=[O:21])[CH2:8][CH:7]([CH2:6][CH2:5][OH:4])[CH2:15]2

Participants

Conditions

Temperature: 20 °C

Procedure

Acetamide 155 (24.0 g, 78 mmol) was suspended in MeOH (350 mL), H2O (180 mL) and cHCl (150 mL), and stirred at reflux temperature for 1 h. The resulting orange solution was cooled to 20° C. and the solvent evaporated to give nitroaniline 156 (17.4 g, 100%) as an orange solid: mp 89-91° C.; 1H NMR δ 7.90 (s, 1H, H-4), 6.62 (s, 1H, H-7), 6.02 (br s, 2H, NH2), 3.74 (t, J=6.6 Hz, 2H, CH2O), 2.96-3.04 (m, 2H, H-1, H-3), 2.49-2.60 (m, 3H, H-1, H-2, H-3), 1.77 (q, J=6.6 Hz, 2H, CH2), 1.40 (br s, 1H, OH); 13C NMR δ 153.4, 144.3, 133.0, 131.2, 120.9, 113.5, 61.7, 39.3, 38.2, 37.7, 37.2. Anal. calcd for C11H14N2O3: C, 59.5; H, 6.4; N, 12.6. Found: C, 59.7; H, 6.3; N, 12.2%.

Workup

temperatureat reflux temperature for 1 h
customthe solvent evaporated

Sources & evidence

ORD record: ord-2c9962e510fe4997bd42fbb5893058ce
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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