Sodium Dithionite → Ethyl 2-amino-2-cyanoacetate

HRID 1185247Notes

Reaction equation

[C:1](/[C:3](=[N:9]\O)/[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])(O)=O.[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+]>O>[NH2:9][CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 35 °C

Procedure

To a stirred solution of (E)-ethyl 2-cyano-2-(hydroxyimino)acetate (20 g, 0.14 mol) in water (250 mL) was added a saturated solution of NaHCO3 in water (160 mL), followed by the addition of Na2S2O4 (60 g, 0.423 mol). The reaction mixture was warmed up to 35° C. and stirred for additional 2 hr. It was then saturated with NaCl (150 g) and extracted with DCM (3×350 mL). Combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give ethyl 2-amino-2-cyanoacetate as a red oil (7.8 g, 43%) that was used at the next step without additional purification. 1H-NMR (CDCl3, 500 MHz) δ (ppm): 4.45 (s, 1H), 4.34 (q, J=7.0 Hz, 2H), 1.36 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 129 [M+H+].

Workup

extractionsaturated with NaCl (150 g) and extracted with DCM (3×350 mL)
washCombined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-10ab444ed5494285a7558a626a29bb0d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669361B2

Reaction notes

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