Diisopropylethylamine → HCID 19068877, compound

HRID 1957126Notes

Reaction equation

[CH3:1][C:2]1[C:8]([CH3:9])=[C:7](I)[C:5]([NH2:6])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(N(C(C)C)C(C)C)C.[O:23]1[CH2:27]CC[CH2:24]1.C[OH:29]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[NH2:6][C:5]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:3][C:2]([CH3:1])=[C:8]([CH3:9])[C:7]=1[C:24]([O:23][CH3:27])=[O:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,5-dimethyl-6-iodo-2-nitroaniline (17.52 g, 60 mmol), bis(triphenylphosphine)palladium (II) chloride (1.75 g) and ethyldiisopropylamine (11.5 mL, 66 mmol) in tetrahydofuran/methanol (1:1, 300 mL) was heated at 100° C. under a carbon monoxide atmosphere (100 psi, 6.7 atm) in an autoclave for 8 hours. After being cooled, the mixture was concentrated under reduced pressure, and the residue was partitioned between dichloromethane (150 mL) and water (150 mL). The aqueous layer was extracted with dichloromethane (2×150 mL), and the combined extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography, eluting with hexane:ethyl acetate (9:1), then (3:1) and finally hexane:dichloromethane (1:1) gave methyl 2-amino-5,6-dimethyl-3-nitrobenzoate (12.94 g, 96%) as an orange solid.

Workup

temperatureAfter being cooled
concentrationthe mixture was concentrated under reduced pressure
customthe residue was partitioned between dichloromethane (150 mL) and water (150 mL)
extractionThe aqueous layer was extracted with dichloromethane (2×150 mL)
dry with materialthe combined extracts were dried (MgSO4)
concentrationconcentrated under reduced pressure
customPurification by flash chromatography
washeluting with hexane:ethyl acetate (9:1)

Sources & evidence

ORD record: ord-5c8accd5278146d4b369f6e502c14f45
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783572

Reaction notes

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