Ammonia → Methyl 4-carbamoyl-2-methoxybenzoate

HRID 59317Notes

Reaction equation

HRID 59317 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[C:6](O)=[O:7].C(Cl)(=O)C(Cl)=O.[NH3:22]>C1COCC1>[C:6]([C:5]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:7])[NH2:22]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 123983053-Methoxy-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 90019463Methyl 4-carbamoyl-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in step-2 of Intermediate-26 by using 3-methoxy-4-(methoxycarbonyl)benzoic acid (2.00 g, 9.52 mmol), oxalyl chloride (1.02 g, 11.42 mmol), ammonia gas and THF (25 mL) to afford 1.40 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.79 (s, 3H), 3.87 (s, 3H), 7.49 (d, J=8.4 Hz, 1H), 7.57 (s, 2H), 7.68 (d, J=7.8 Hz, 1H), 8.14 (s, 1H); MS (m/z): 209.99 (M)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cfb5e065b0bf4565b4234929aa282110
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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