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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1747417Generated: October 31, 2026

Acetic Acid → HCID 59497326, compound

https://huagongshe.com/reaction/1747417

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantO-PhenylenediamineHCID 7243—
ReactantMethyl 4-methoxyacetoacetateHCID 123500—
ReactantSodium BicarbonateHCID 516892—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductHCID 59497326HCID 5949732627%

Reaction Steps

4-Methoxy-3-oxo-butyric acid methyl ester (0.67 mL, 5.0 mmol) and Benzene-1,2-diamine (560 mg, 5.5 mmol) are dissolved in DCM (20 mL) and HOAc (0.63 mL, 11 mmol) is added into it. The mixture is stirred for 6 hrs and then NaBH(OAC)3 (3.7 g, 17 mmol) is added and the mixture is stirred for another 60 hr. Then 50 mL of sat. NaHCO3 along with 50 mL of water are added and the mixture is extracted with EtOAc (3×100 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column choromatography affords 320 mg (27%) of 3-(2-Amino-phenylamino)-4-methoxy-butyric acid methyl ester.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150556B2
Source datasetuspto-grants-2015_10
ORD IDord-6d41e224b94e4e179622ed9190570c70
Source noteuspto-grants-2015_10