Hydrochloric Acid → HCID 178419951, compound

HRID 17773

Reaction equation

HRID 17773 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[NH2:13][C:14]1[CH:22]=[CH:21][C:17]2[NH:18][N:19]=[N:20][C:16]=2[CH:15]=1.C([BH3-])#N.[Na+].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.Cl.[OH-].[Na+]>CO.C(OCC)(=O)C.C(O)(=O)C>[NH:18]1[C:17]2[CH:21]=[CH:22][C:14]([NH:13][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)=[CH:15][C:16]=2[N:20]=[N:19]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 62012-NaphthalenecarboxaldehydeHCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 178507366HCID 178507366, compound

Product 1

HCID 178419951HCID 178419951, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The general procedure employed was as follows. Naphthalene-2-carbaldehyde (624 mg, 4 mmol) in methanol (25 ml) was added to a solution of 5-amino-1H-benzotriazole in methanol (25 ml) that had been adjusted to pH 6 by the addition of glacial acetic acid (1 ml). Sodium cyanoborohydride (1.89 g, 30 mmol) was added and the resulting mixture was stirred at room temperature overnight by which time TLC (A) and ninhydrin development indicated the conversion of starting materials. Hydrochloric acid (50% HCl/H2O, 5 ml) was added and the solution was neutralised to pH 7 by addition of NaOH (1M). Methanol was removed in vacuo to afford an aqueous residue that was dissolved in ethyl acetate (50 ml) and extracted with sodium chloride solution (4×20 ml). Purification by column chromatography, eluting with methanol (0-10%) in dichloromethane afforded [11] as a pale yellow oil. Trituration from diethyl ether afforded [11] as a white solid (880 mg, 80%). Rf (A) 0.42 δH(400 MHz; DMSO-d6 {D2O shake}) 4.50 (2H, s, CH2) 6.45 (1H, s, BT) 6.89 (1H, s, NH, disappeared) 6.91 (1H, d, J8.9, BT) 7.43-7.49 (2H, m, Ar—H) 7.54 (1H, d, J8.6, Nap) 7.65 (1H, d, J8.9, BT) 7.82-7.89 (4H, m, Nap) 14.72 (1H, s, NH, disappeared); m/z (EI−HR) 274.12177 [(M calc. for C17H14N4 274.12185].

Workup

  1. customMethanol was removed in vacuo
  2. customto afford an aqueous residue that
  3. extractionextracted with sodium chloride solution (4×20 ml)
  4. customPurification by column chromatography
  5. washeluting with methanol (0-10%) in dichloromethane

Sources & evidence

ORD record
ord-896c9e2083b64c08afbc5c66a9f8a6ba
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Linked notes

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