2,2,2-Trifluoroacetaldehyde hydrate → HCID 16659312, compound

HRID 990927Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].O.[F:15][C:16]([F:20])([F:19])[CH:17]=O.[BH3-]C#N.[Na+]>>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:17][C:16]([F:20])([F:19])[F:15])[CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 3

HCID 27813662,2,2-Trifluoroacetaldehyde hydrate

HCID 5003444Sodium cyanoborohydride

HCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 16659312HCID 16659312, compoundYield 90.8%

Procedure

This compound was prepared by General Method 7 from 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (EXAMPLE 1) (388 mg, 2.1 mmol), 2,2,2-trifluoroacetaldehyde monohydrate (2.51 g, 21.6 mmol) and NaBH3CN (656 mg, 10.4 mmol) to afford 500 mg (88%) of 3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine, a yellow solid. Data for 3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine: Rf 0.59 (3:2 EtOAc:hexanes); 1H NMR (400 MHz, CDCl3) δ 7.81 (dd, 1H, J=8.8, 2.6), 7.72 (d, 1H, J=2.6), 6.72 (d, 1H, J=9.1), 4.27 (t, 2H, J=4.5), 3.94 (2H, J=8.6), 3.61 (t, 2H, J=4.5).

Sources & evidence

ORD record: ord-a58770ffb54f4c64afde5e344e981fdd
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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