Dimethylformamide dimethyl acetal → HCID 86594636, compound

HRID 585769Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][CH2:14][CH3:15])=[CH:6][C:5]=1[NH2:16].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>O>[CH3:20][N:21]([CH:23]=[N:16][C:5]1[CH:6]=[C:7]([O:13][CH2:14][CH3:15])[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:17])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A 3-L round-bottomed flask under N2 equipped with an overhead stirrer, a condenser and a thermocouple is charged with 2-amino-4-ethoxy-5-nitrobenzoic acid methyl ester (80 g, 333 mmol) and N,N-dimethylformamide dimethyl acetal (500 mL). The reaction mixture is heated to reflux (100° C.). Once the thick slurry becomes homogeneous and the reaction is complete, the reaction mixture is cooled to 25 to 30° C. The reaction mixture is diluted with water (3 L) and the resulting suspension is filtered. The filter cake is washed with water (3×500 mL) and dried under vacuum (50 mm Hg) at 55° C. to provide the title compound as an off-white solid (89.6 g, 91% yield, >90% purity by NMR integration). 1H NMR (300 MHz, DMSO-d6): 8.23 (s, 1H), 7.81 (s, 1H), 6.71 (s, 1H), 4.22 (q, J=7 Hz), 3.68 (s, 3H), 3.09 (s, 3H), 2.97 (s, 3H), 1.40 (t, J=7 Hz, 3H).

Workup

customA 3-L round-bottomed flask under N2 equipped with an overhead stirrer, a condenser
temperatureThe reaction mixture is heated
temperaturethe reaction mixture is cooled to 25 to 30° C
filtrationthe resulting suspension is filtered
washThe filter cake is washed with water (3×500 mL)
customdried under vacuum (50 mm Hg) at 55° C.

Sources & evidence

ORD record: ord-4ce4fc69a2df44dbb1b09c4804fd8697
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933388B2

Reaction notes

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